Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene

Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene g...

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Published inAdvanced synthesis & catalysis Vol. 360; no. 14; pp. 2678 - 2690
Main Authors Barlow, Helen, Buser, Jonas Y., Glauninger, Hendrik, Luciani, Carla V., Martinelli, Joseph R., Oram, Niall, Thompson‐Van Hook, Nichole, Richardson, Jeffery
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 16.07.2018
Wiley Subscription Services, Inc
Subjects
Antioxidants
Aromatic compounds
Bromides
Catalysis
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
cross-coupling
Ethylene
ethylene solubility
Heck reaction
Physical Sciences
Pterostilbene
Science & Technology
stilbene
Substrates
unsymmetrical
HALIDES
PALLADIUM
STYRENES
unsymmetrical
STRATEGY
ARYLATION
Heck reaction
ethylene
Pterostilbene
PRESSURE
OLEFINATION
ethylene solubility
cross-coupling
stilbene
CHEMISTRY
EFFICIENT
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Abstract Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model‐aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene.
AbstractList Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and modelaided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene.
Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model‐aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene.
Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two‐step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model‐aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. magnified image
Author Luciani, Carla V.
Richardson, Jeffery
Thompson‐Van Hook, Nichole
Barlow, Helen
Buser, Jonas Y.
Glauninger, Hendrik
Oram, Niall
Martinelli, Joseph R.
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Cites_doi 10.1021/jo800235c
10.1039/c001980a
10.1002/aoc.1756
10.1002/anie.201206346
10.1002/ejoc.200900634
10.3109/10408363.2013.805182
10.1055/s-2006-942471
10.1021/jo025868h
10.1016/j.tet.2009.11.017
10.1002/anie.201400474
10.1002/chem.201101174
10.1021/acs.oprd.5b00406
10.1055/s-0031-1289291
10.1016/j.ejphar.2016.07.046
10.1016/j.tetlet.2010.09.050
10.1021/cr9903048
10.1016/j.jorganchem.2008.11.065
10.1039/c4cc00055b
10.1002/anie.201107261
10.1021/ja210223s
10.1002/cctc.201200778
10.1021/acs.jmedchem.6b01026
10.1016/S0040-4020(01)00665-2
10.1002/9783527628087
10.1080/00397919908085894
10.1016/S1381-1169(99)00121-1
10.1039/C4CC00055B
10.1021/jo00406a033
10.1016/1381-1169(94)00077-8
10.1039/JR9530002889
10.2174/0929867323666160517121629
10.1039/b100328n
10.1002/(SICI)1521-3773(19980302)37:4<481::AID-ANIE481>3.0.CO;2-I
10.1021/om00018a037
10.1002/jhet.5570270544
10.1139/v01-033
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Issue 14
Keywords HALIDES
PALLADIUM
STYRENES
unsymmetrical
STRATEGY
ARYLATION
Heck reaction
ethylene
Pterostilbene
PRESSURE
OLEFINATION
ethylene solubility
cross-coupling
stilbene
CHEMISTRY
EFFICIENT
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References 1995; 97
2017; 60
2011
2016; 789
1999; 29
2009
2009; 694
1953
2006
1999; 147
2011; 17
2005; 27
2008; 73
2013; 5
2011; 133
2012; 51
1998; 37
2010; 66
2010; 46
2001
1990; 27
1978; 43
2002; 67
2013; 50
2016; 20
1994; 13
2000; 100
2011; 25
2001; 57
2001; 79
2014; 50
2010; 51
2016; 23
2014; 53
PLEVYAK, JE (WOS:A1978FC53300033) 1978; 43
Petuskova, J (WOS:000298571600026) 2011; 133
Das, JP (WOS:000178820200040) 2002; 67
Estrela, JM (WOS:000418393100001) 2017; 60
Saiyed, AS (WOS:000284303200005) 2010; 51
Sharma, N (WOS:000295457700020) 2011; 17
Heck, R. F. (000438710200012.17) 2005; 27
Bourne, SL (WOS:000314238400018) 2013; 5
Bourne, SL (WOS:000296746800006) 2011
Kotzner, L (WOS:000335476400038) 2014; 53
Buser, JY (WOS:000333522700024) 2014; 50
Sharma, A (WOS:000277318000013) 2010; 46
IZUMI, T (WOS:A1990DV62600044) 1990; 27
Kormos, CM (WOS:000255698500026) 2008; 73
Smith, CR (WOS:000274766900016) 2010; 66
Beletskaya, IP (WOS:000088838500011) 2000; 100
McNulty, J (WOS:000269221800002) 2009; 2009
KIJI, JS (WOS:A1995RF52300002) 1995; 97
Reetz, MT (WOS:000072421500014) 1998; 37
FREUND, W (WOS:A1953UB69000005) 1953
Elisa, G. (000438710200012.12) 2016; 23
Shard, A (WOS:000311706500018) 2012; 51
DEVRIES, RA (WOS:A1994NR47800037) 1994; 13
Kiji, J (WOS:000083978400002) 1999; 147
Abrams, ML (WOS:000376473400005) 2016; 20
Kosuru, R (WOS:000385327500027) 2016; 789
Atla, SB (WOS:000263365600013) 2009; 694
de Vries, JG (WOS:000170070900081) 2001; 79
(000438710200012.1) 2002
Likhtenshtein, G. (000438710200012.25) 2009
Estrela, JM (WOS:000322254900001) 2013; 50
Whitcombe, NJ (WOS:000170631700002) 2001; 57
Durantini, EN (WOS:000083338300014) 1999; 29
Kumar, R (WOS:000301173800015) 2012; 51
Southard, GE (WOS:000239924200002) 2006
Nobre, SM (WOS:000288806300007) 2011; 25
Gibson, S (WOS:000168356500047) 2001
e_1_2_6_32_1
e_1_2_6_10_1
e_1_2_6_30_2
Southard G. E. (e_1_2_6_21_2) 2006
e_1_2_6_18_2
e_1_2_6_19_2
e_1_2_6_12_2
Bourne S. L. (e_1_2_6_31_2) 2011
e_1_2_6_36_1
e_1_2_6_13_2
e_1_2_6_34_2
e_1_2_6_35_1
e_1_2_6_33_2
e_1_2_6_11_2
e_1_2_6_16_2
e_1_2_6_17_1
e_1_2_6_39_1
e_1_2_6_14_2
e_1_2_6_38_1
e_1_2_6_15_2
e_1_2_6_37_1
e_1_2_6_42_2
e_1_2_6_43_1
e_1_2_6_20_2
e_1_2_6_41_2
e_1_2_6_40_1
Heck R. F. (e_1_2_6_22_2) 2005; 27
e_1_2_6_8_2
e_1_2_6_9_2
e_1_2_6_4_2
e_1_2_6_6_2
e_1_2_6_7_1
e_1_2_6_5_2
e_1_2_6_24_2
e_1_2_6_48_1
e_1_2_6_23_2
e_1_2_6_3_1
e_1_2_6_2_1
e_1_2_6_29_1
e_1_2_6_44_1
e_1_2_6_28_1
e_1_2_6_45_1
e_1_2_6_27_1
e_1_2_6_46_1
e_1_2_6_25_2
e_1_2_6_26_1
e_1_2_6_47_1
References_xml – volume: 50
  start-page: 65
  year: 2013
  end-page: 78
  publication-title: Crit. Rev. Clin. Lab. Sci.
– volume: 17
  start-page: 10350
  year: 2011
  end-page: 10356
  publication-title: Chem. Eur. J.
– year: 2009
– volume: 27
  start-page: 345
  year: 2005
  end-page: 390
  publication-title: Organic Reactions.
– volume: 133
  start-page: 20758
  year: 2011
  publication-title: J. Am. Chem. Soc.
– volume: 73
  start-page: 3854
  year: 2008
  end-page: 3858
  publication-title: J. Org. Chem.
– volume: 789
  start-page: 229
  year: 2016
  end-page: 243
  publication-title: Eur. J. Pharm.
– start-page: 2475
  year: 2006
  end-page: 2477
  publication-title: Synthesis
– volume: 46
  start-page: 3283
  year: 2010
  end-page: 3285
  publication-title: Chem. Commun.
– volume: 57
  start-page: 7449
  year: 2001
  end-page: 7476
  publication-title: Tetrahedron
– volume: 51
  start-page: 6227
  year: 2010
  end-page: 6231
  publication-title: Tetrahedron Lett.
– start-page: 4031
  year: 2009
  end-page: 4035
  publication-title: Eur. J. Org. Chem.
– volume: 100
  start-page: 3009
  year: 2000
  end-page: 3066
  publication-title: Chem. Rev.
– volume: 29
  start-page: 4201
  year: 1999
  end-page: 4222
  publication-title: Synth. Commun.
– volume: 51
  start-page: 2636
  year: 2012
  end-page: 2639
  publication-title: Angew. Chem. Int. Ed.
– volume: 43
  start-page: 2454
  year: 1978
  end-page: 2456
  publication-title: J. Org. Chem.
– volume: 25
  start-page: 289
  year: 2011
  end-page: 293
  publication-title: Appl. Organomet. Chem.
– start-page: 2643
  year: 2011
  end-page: 2647
  publication-title: Synlett
– volume: 53
  start-page: 5202
  year: 2014
  end-page: 5205
  publication-title: Angew. Chem. Int. Ed.
– start-page: 779
  year: 2001
  end-page: 780
  publication-title: Chem. Commun.
– volume: 66
  start-page: 1102
  year: 2010
  end-page: 1110
  publication-title: Tetrahedron
– volume: 50
  start-page: 4234
  year: 2014
  end-page: 4237
  publication-title: Chem. Commun.
– volume: 20
  start-page: 901
  year: 2016
  end-page: 910
  publication-title: Org. Process Res. Dev.
– start-page: 2889
  year: 1953
  end-page: 2891
  publication-title: J. Chem. Soc.
– volume: 694
  start-page: 683
  year: 2009
  end-page: 690
  publication-title: J. Organomet. Chem.
– volume: 79
  start-page: 1086
  year: 2001
  end-page: 1092
  publication-title: Can. J. Chem.
– volume: 51
  start-page: 12250
  year: 2012
  end-page: 12253
  publication-title: Angew. Chem. Int. Ed.
– volume: 147
  start-page: 3
  year: 1999
  end-page: 10
  publication-title: J. Mol. Catal. A
– volume: 37
  start-page: 481
  year: 1998
  end-page: 483
  publication-title: Angew. Chem. Int. Ed.
– volume: 5
  start-page: 159
  year: 2013
  end-page: 172
  publication-title: ChemCatChem
– volume: 27
  start-page: 1419
  year: 1990
  end-page: 1424
  publication-title: J. Heterocycl. Chem.
– volume: 67
  start-page: 7861
  year: 2002
  end-page: 7864
  publication-title: J. Org. Chem.
– volume: 97
  start-page: 73
  year: 1995
  end-page: 77
  publication-title: J. Mol. Catal. A
– volume: 23
  start-page: 2439
  year: 2016
  end-page: 2489
  publication-title: Curr. Med. Chem.
– volume: 13
  start-page: 2405
  year: 1994
  end-page: 2411
  publication-title: Organometallics
– volume: 60
  start-page: 9413
  year: 2017
  end-page: 9436
  publication-title: J. Med. Chem.
– volume: 73
  start-page: 3854
  year: 2008
  ident: WOS:000255698500026
  article-title: Preparation of nonsymmetrically substituted stilbenes in a one-pot two-step Heck strategy using ethene as a reagent
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo800235c
  contributor:
    fullname: Kormos, CM
– start-page: 2889
  year: 1953
  ident: WOS:A1953UB69000005
  article-title: THE REACTION OF DIAZONIUM SALTS WITH BETA-2-THIENYLACRYLIC ACID
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY
  contributor:
    fullname: FREUND, W
– year: 2002
  ident: 000438710200012.1
– volume: 46
  start-page: 3283
  year: 2010
  ident: WOS:000277318000013
  article-title: Direct olefination of benzaldehydes into hydroxy functionalized oligo (p-phenylenevinylene)s via Pd-catalyzed heterodomino Knoevenagel-decarboxylation- Heck sequence and its application for fluoride sensing pi-conjugated units
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c001980a
  contributor:
    fullname: Sharma, A
– volume: 25
  start-page: 289
  year: 2011
  ident: WOS:000288806300007
  article-title: The synthesis of non-symmetrical stilbene analogs of trans-resveratrol using the same Pd catalyst in a sequential double-Heck arylation of ethylene
  publication-title: APPLIED ORGANOMETALLIC CHEMISTRY
  doi: 10.1002/aoc.1756
  contributor:
    fullname: Nobre, SM
– volume: 27
  start-page: 345
  year: 2005
  ident: 000438710200012.17
  publication-title: Organic Reactions.
  contributor:
    fullname: Heck, R. F.
– volume: 51
  start-page: 12250
  year: 2012
  ident: WOS:000311706500018
  article-title: Tandem Heck/Decarboxylation/Heck Strategy: Protecting-Group-Free Synthesis of Symmetric and Unsymmetric Hydroxylated Stilbenoids
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201206346
  contributor:
    fullname: Shard, A
– volume: 2009
  start-page: 4031
  year: 2009
  ident: WOS:000269221800002
  article-title: Highly Stereoselective and General Synthesis of (E)-Stilbenes and Alkenes by Means of an Aqueous Wittig Reaction
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.200900634
  contributor:
    fullname: McNulty, J
– volume: 50
  start-page: 65
  year: 2013
  ident: WOS:000322254900001
  article-title: Pterostilbene: Biomedical applications
  publication-title: CRITICAL REVIEWS IN CLINICAL LABORATORY SCIENCES
  doi: 10.3109/10408363.2013.805182
  contributor:
    fullname: Estrela, JM
– start-page: 2475
  year: 2006
  ident: WOS:000239924200002
  article-title: Heck cross-coupling for synthesizing metal-complexing monomers
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-2006-942471
  contributor:
    fullname: Southard, GE
– volume: 13
  start-page: 2405
  year: 1994
  ident: WOS:A1994NR47800037
  article-title: SYNTHESIS OF HIGH-PURITY O-VINYLTOLUENE AND P-VINYLTOLUENE BY THE HECK PALLADIUM-CATALYZED ARYLATION REACTION
  publication-title: ORGANOMETALLICS
  contributor:
    fullname: DEVRIES, RA
– volume: 79
  start-page: 1086
  year: 2001
  ident: WOS:000170070900081
  article-title: The Heck reaction in the production of fine chemicals
  publication-title: CANADIAN JOURNAL OF CHEMISTRY
  contributor:
    fullname: de Vries, JG
– volume: 57
  start-page: 7449
  year: 2001
  ident: WOS:000170631700002
  article-title: Advances in the Heck chemistry of aryl bromides and chlorides
  publication-title: TETRAHEDRON
  contributor:
    fullname: Whitcombe, NJ
– start-page: 779
  year: 2001
  ident: WOS:000168356500047
  article-title: Highly efficient C-C coupling reactions using metallated benzylphosphine complexes of palladium
  publication-title: CHEMICAL COMMUNICATIONS
  contributor:
    fullname: Gibson, S
– volume: 67
  start-page: 7861
  year: 2002
  ident: WOS:000178820200040
  article-title: Catalytic hunsdiecker reaction of alpha,beta-unsaturated carboxylic acids: How efficient is the catalyst?
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo025868h
  contributor:
    fullname: Das, JP
– volume: 23
  start-page: 2439
  year: 2016
  ident: 000438710200012.12
  publication-title: Curr. Med. Chem.
  contributor:
    fullname: Elisa, G.
– volume: 66
  start-page: 1102
  year: 2010
  ident: WOS:000274766900016
  article-title: Low pressure vinylation of aryl and vinyl halides via Heck-Mizoroki reactions using ethylene
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2009.11.017
  contributor:
    fullname: Smith, CR
– volume: 37
  start-page: 481
  year: 1998
  ident: WOS:000072421500014
  article-title: A new catalyst system for the Heck reaction of unreactive aryl halides
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  contributor:
    fullname: Reetz, MT
– volume: 53
  start-page: 5202
  year: 2014
  ident: WOS:000335476400038
  article-title: Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201400474
  contributor:
    fullname: Kotzner, L
– volume: 43
  start-page: 2454
  year: 1978
  ident: WOS:A1978FC53300033
  article-title: PALLADIUM-CATALYZED ARYLATION OF ETHYLENE
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: PLEVYAK, JE
– year: 2009
  ident: 000438710200012.25
  publication-title: Stilbenes: Applications in Chemistry, Life Sciences and Materials Science
  contributor:
    fullname: Likhtenshtein, G.
– volume: 147
  start-page: 3
  year: 1999
  ident: WOS:000083978400002
  article-title: Palladium-catalyzed arylation of ethylene. A synthetic route to styrenes, stilbenes, and poly(phenylene vinylene)s
  publication-title: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
  contributor:
    fullname: Kiji, J
– volume: 17
  start-page: 10350
  year: 2011
  ident: WOS:000295457700020
  article-title: Pd-Catalyzed Orthogonal Knoevenagel/Perkin Condensation-Decarboxylation-Heck/Suzuki Sequences: Tandem Transformations of Benzaldehydes into Hydroxy-Functionalized Antidiabetic Stilbene-Cinnamoyl Hybrids and Asymmetric Distyrylbenzenes
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201101174
  contributor:
    fullname: Sharma, N
– volume: 27
  start-page: 1419
  year: 1990
  ident: WOS:A1990DV62600044
  article-title: PALLADIUM-CATALYZED SYNTHESIS OF ISOCOUMARIN AND 1-ISOQUINOLINONE DERIVATIVES
  publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY
  contributor:
    fullname: IZUMI, T
– volume: 29
  start-page: 4201
  year: 1999
  ident: WOS:000083338300014
  article-title: Synthesis of functional olefins using the Wittig-Horner reaction in different media
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: Durantini, EN
– volume: 20
  start-page: 901
  year: 2016
  ident: WOS:000376473400005
  article-title: Continuous Liquid Vapor Reactions Part 2: Asymmetric Hydroformylation with Rhodium-Bisdiazaphos Catalysts in a Vertical Pipes-in-Series Reactor
  publication-title: ORGANIC PROCESS RESEARCH & DEVELOPMENT
  doi: 10.1021/acs.oprd.5b00406
  contributor:
    fullname: Abrams, ML
– start-page: 2643
  year: 2011
  ident: WOS:000296746800006
  article-title: The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction
  publication-title: SYNLETT
  doi: 10.1055/s-0031-1289291
  contributor:
    fullname: Bourne, SL
– volume: 789
  start-page: 229
  year: 2016
  ident: WOS:000385327500027
  article-title: Promising therapeutic potential of pterostilbene and its mechanistic insight based on preclinical evidence
  publication-title: EUROPEAN JOURNAL OF PHARMACOLOGY
  doi: 10.1016/j.ejphar.2016.07.046
  contributor:
    fullname: Kosuru, R
– volume: 51
  start-page: 6227
  year: 2010
  ident: WOS:000284303200005
  article-title: One-pot synthesis of stilbenes by dehydrohalogenation-Heck olefination and multicomponent Wittig-Heck reaction
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2010.09.050
  contributor:
    fullname: Saiyed, AS
– volume: 97
  start-page: 73
  year: 1995
  ident: WOS:A1995RF52300002
  article-title: PALLADIUM-CATALYZED, ARYLATION OF ETHYLENE (THE HECK REACTION) UNDER AQUEOUS CONDITIONS
  publication-title: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
  contributor:
    fullname: KIJI, JS
– volume: 100
  start-page: 3009
  year: 2000
  ident: WOS:000088838500011
  article-title: The heck reaction as a sharpening stone of palladium catalysis
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr9903048
  contributor:
    fullname: Beletskaya, IP
– volume: 694
  start-page: 683
  year: 2009
  ident: WOS:000263365600013
  article-title: NC palladacycles in the Heck arylation of ethylene: Synthesis, structure and their reactivity
  publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  doi: 10.1016/j.jorganchem.2008.11.065
  contributor:
    fullname: Atla, SB
– volume: 50
  start-page: 4234
  year: 2014
  ident: WOS:000333522700024
  article-title: Reaction characterization by flow NMR: quantitation and monitoring of dissolved H-2 via flow NMR at high pressure
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c4cc00055b
  contributor:
    fullname: Buser, JY
– volume: 51
  start-page: 2636
  year: 2012
  ident: WOS:000301173800015
  article-title: Palladium-Catalyzed Dehydrative Heck Olefination of Secondary Aryl Alcohols in Ionic Liquids: Towards a Waste-Free Strategy for Tandem Synthesis of Stilbenoids
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201107261
  contributor:
    fullname: Kumar, R
– volume: 133
  start-page: 20758
  year: 2011
  ident: WOS:000298571600026
  article-title: Synthesis, Structure, and Reactivity of Carbene-Stabilized Phosphorus(III)-Centered Trications [L3P](3+)
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja210223s
  contributor:
    fullname: Petuskova, J
– volume: 5
  start-page: 159
  year: 2013
  ident: WOS:000314238400018
  article-title: Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
  publication-title: CHEMCATCHEM
  doi: 10.1002/cctc.201200778
  contributor:
    fullname: Bourne, SL
– volume: 60
  start-page: 9413
  year: 2017
  ident: WOS:000418393100001
  article-title: Polyphenolic Phytochemicals in Cancer Prevention and Therapy: Bioavailability versus Bioefficacy
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/acs.jmedchem.6b01026
  contributor:
    fullname: Estrela, JM
– ident: e_1_2_6_5_2
  doi: 10.1016/S0040-4020(01)00665-2
– ident: e_1_2_6_12_2
  doi: 10.1039/c001980a
– ident: e_1_2_6_28_1
  doi: 10.1002/aoc.1756
– ident: e_1_2_6_11_2
  doi: 10.1002/chem.201101174
– ident: e_1_2_6_40_1
– ident: e_1_2_6_29_1
– ident: e_1_2_6_2_1
  doi: 10.1002/9783527628087
– ident: e_1_2_6_45_1
  doi: 10.1080/00397919908085894
– ident: e_1_2_6_27_1
  doi: 10.1021/ja210223s
– ident: e_1_2_6_39_1
  doi: 10.1021/acs.jmedchem.6b01026
– ident: e_1_2_6_7_1
– ident: e_1_2_6_34_2
  doi: 10.1016/S1381-1169(99)00121-1
– ident: e_1_2_6_36_1
– ident: e_1_2_6_15_2
  doi: 10.1016/j.tetlet.2010.09.050
– ident: e_1_2_6_8_2
  doi: 10.1021/acs.oprd.5b00406
– ident: e_1_2_6_9_2
– ident: e_1_2_6_42_2
  doi: 10.1016/j.ejphar.2016.07.046
– ident: e_1_2_6_17_1
– ident: e_1_2_6_47_1
  doi: 10.1021/jo800235c
– ident: e_1_2_6_37_1
  doi: 10.1039/C4CC00055B
– ident: e_1_2_6_13_2
  doi: 10.1021/jo025868h
– start-page: 2475
  year: 2006
  ident: e_1_2_6_21_2
  publication-title: Synthesis
  contributor:
    fullname: Southard G. E.
– ident: e_1_2_6_14_2
  doi: 10.1002/ejoc.200900634
– ident: e_1_2_6_46_1
  doi: 10.1002/anie.201107261
– ident: e_1_2_6_25_2
  doi: 10.1021/jo00406a033
– ident: e_1_2_6_43_1
  doi: 10.1002/anie.201206346
– ident: e_1_2_6_10_1
– ident: e_1_2_6_33_2
  doi: 10.1016/1381-1169(94)00077-8
– ident: e_1_2_6_48_1
  doi: 10.1039/JR9530002889
– ident: e_1_2_6_16_2
  doi: 10.1002/anie.201206346
– ident: e_1_2_6_35_1
  doi: 10.1016/j.tet.2009.11.017
– ident: e_1_2_6_41_2
  doi: 10.3109/10408363.2013.805182
– ident: e_1_2_6_38_1
  doi: 10.2174/0929867323666160517121629
– ident: e_1_2_6_32_1
– ident: e_1_2_6_3_1
– ident: e_1_2_6_18_2
  doi: 10.1016/j.jorganchem.2008.11.065
– ident: e_1_2_6_20_2
  doi: 10.1039/b100328n
– ident: e_1_2_6_4_2
  doi: 10.1021/cr9903048
– ident: e_1_2_6_24_2
  doi: 10.1002/(SICI)1521-3773(19980302)37:4<481::AID-ANIE481>3.0.CO;2-I
– ident: e_1_2_6_19_2
  doi: 10.1021/om00018a037
– volume: 27
  start-page: 345
  year: 2005
  ident: e_1_2_6_22_2
  publication-title: Organic Reactions.
  contributor:
    fullname: Heck R. F.
– start-page: 2643
  year: 2011
  ident: e_1_2_6_31_2
  publication-title: Synlett
  contributor:
    fullname: Bourne S. L.
– ident: e_1_2_6_23_2
  doi: 10.1002/jhet.5570270544
– ident: e_1_2_6_26_1
  doi: 10.1021/jo800235c
– ident: e_1_2_6_6_2
  doi: 10.1139/v01-033
– ident: e_1_2_6_44_1
  doi: 10.1002/anie.201400474
– ident: e_1_2_6_30_2
  doi: 10.1002/cctc.201200778
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Snippet Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a...
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SubjectTerms Antioxidants
Aromatic compounds
Bromides
Catalysis
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
cross-coupling
Ethylene
ethylene solubility
Heck reaction
Physical Sciences
Pterostilbene
Science & Technology
stilbene
Substrates
unsymmetrical
Title Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene
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