Radical‐Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes

Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopr...

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Published inAdvanced synthesis & catalysis Vol. 362; no. 1; pp. 242 - 247
Main Authors Milligan, John A., Burns, Kevin L., Le, Anthony V., Polites, Viktor C., Wang, Zheng‐Jun, Molander, Gary A., Kelly, Christopher B.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.01.2020
Wiley Subscription Services, Inc
Subjects
Alkenes
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Crossovers
Cyclization
Cyclopropanes
Embedded systems
Organic compounds
Photoredox Catalysis
Physical Sciences
Radical/Polar Crossover
Radicals
Science & Technology
Substitution reactions
Photoredox Catalysis
ALKYLATION
Cyclopropanes
ENABLES
Radical
Radicals
DISCOVERY
ALKENES
Polar Crossover
POTENT
Cyclization
CONSTRUCTION
GENERATION
CATALYZED CYCLOPROPANATION
Online AccessGet full text
ISSN1615-4150
1615-4169
DOI10.1002/adsc.201901051

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Abstract Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox‐enabled Giese‐type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.
AbstractList Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox-enabled Giese-type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox-enabled Giese-type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.
Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox‐enabled Giese‐type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.
Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox‐enabled Giese‐type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group. magnified image
Author Burns, Kevin L.
Milligan, John A.
Polites, Viktor C.
Molander, Gary A.
Le, Anthony V.
Wang, Zheng‐Jun
Kelly, Christopher B.
AuthorAffiliation b Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, P.O. Box 842006, Richmond, Virginia 23284, USA
a Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA
d State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 41000, China
c Medicines for All Institute, Virginia Commonwealth University, Biotech 8, 737 North Fifth Street, Richmond, Virginia, 23219, USA
AuthorAffiliation_xml – name: b Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, P.O. Box 842006, Richmond, Virginia 23284, USA
– name: c Medicines for All Institute, Virginia Commonwealth University, Biotech 8, 737 North Fifth Street, Richmond, Virginia, 23219, USA
– name: a Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA
– name: d State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 41000, China
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Cites_doi 10.1021/ja1084749
10.1021/acscatal.6b03665
10.1021/acscatal.7b00094
10.1021/acs.orglett.8b02968
10.1039/C39730000548
10.1021/acscatal.5b02204
10.1002/ejoc.200500143
10.1039/C8SC05558K
10.1021/jacs.6b08856
10.1002/anie.201811858
10.1039/C4QO00232F
10.1021/cr010007e
10.15227/orgsyn.094.0016
10.1021/acs.accounts.6b00259
10.1021/acs.jmedchem.6b00472
10.1021/jm500537u
10.1021/jm1006269
10.1002/anie.201710707
10.1021/jm4016894
10.1002/anie.201709487
10.1002/adsc.201900708
10.1021/ja01069a054
10.1016/j.tet.2008.04.079
10.1021/acs.orglett.7b03374
10.1021/jacs.8b05243
10.1021/acs.orglett.9b00602
10.1055/s-0033-1340838
10.1021/jo01343a018
10.1002/anie.201808598
10.1039/B307289B
10.1002/adsc.201800761
10.1055/s-0037-1611872
10.1039/C4CS00304G
10.1039/C8CC07060A
10.1021/jo0401772
10.1039/c4cs00304g
10.1021/jm5005336
10.1039/c8cc07060a
10.1039/c8sc05558k
10.1039/b307289b
10.1039/c4qo00232f
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Issue 1
Keywords Photoredox Catalysis
ALKYLATION
Cyclopropanes
ENABLES
Radical
Radicals
DISCOVERY
ALKENES
Polar Crossover
POTENT
Cyclization
CONSTRUCTION
GENERATION
CATALYZED CYCLOPROPANATION
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References 2017; 7
2015; 58
2010; 53
2018; 140
2018; 360
2019; 51
2019; 10
2004; 69
2019; 58
1996
2014; 46
1973
1964; 86
2005
2019; 361
2016; 59
2018; 20
1966; 31
2014; 1
2017; 94
2016; 6
2019; 21
2015; 44
2017; 56
2010; 132
2014; 57
2017; 19
2016; 138
2008; 64
2003; 1
2003; 103
2018; 54
2016; 49
2001; 58
2018; 57
e_1_2_6_10_1
e_1_2_6_30_2
e_1_2_6_31_1
e_1_2_6_19_2
e_1_2_6_36_1
e_1_2_6_34_2
e_1_2_6_35_1
e_1_2_6_11_1
e_1_2_6_33_2
e_1_2_6_12_1
e_1_2_6_32_2
e_1_2_6_16_2
e_1_2_6_39_2
Rappoport Z. (e_1_2_6_3_2) 1996
e_1_2_6_17_2
e_1_2_6_18_1
e_1_2_6_38_2
e_1_2_6_14_2
e_1_2_6_15_1
e_1_2_6_37_1
e_1_2_6_42_2
e_1_2_6_20_2
e_1_2_6_41_2
e_1_2_6_40_2
Charette A. B. (e_1_2_6_13_2) 2001; 58
e_1_2_6_9_1
e_1_2_6_7_2
e_1_2_6_8_1
e_1_2_6_29_2
e_1_2_6_4_2
e_1_2_6_6_2
e_1_2_6_5_2
e_1_2_6_24_2
e_1_2_6_23_2
e_1_2_6_2_1
e_1_2_6_21_2
e_1_2_6_22_1
e_1_2_6_28_2
e_1_2_6_43_2
e_1_2_6_44_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
Bonnaud, B (WOS:000231025500024) 2005; 2005
Talele, TT (WOS:000385607100004) 2016; 59
Patel, NR (WOS:000395726500032) 2017; 7
Zhu, JB (WOS:000364430400002) 2014; 1
Arora, A (WOS:000385908100023) 2016; 49
Shu, C (WOS:000453344500021) 2018; 57
Herraiz, AG (WOS:000479153600005) 2019; 51
Bartoli, G (WOS:000336838900001) 2014; 46
Rappoport, Z. (000498944300001.30) 1996
Park, EJ (WOS:000224143000048) 2004; 69
Gentles, RG (WOS:000333005800017) 2014; 57
Vacher, B (WOS:000282544800016) 2010; 53
Appel, R (WOS:000285429800042) 2010; 132
Lebel, H (WOS:000182150900003) 2003; 103
FRYE, CL (WOS:A19643125B00017) 1964; 86
GHATAK, UR (WOS:A1973Q357600036) 1973
Matsui, JK (WOS:000398986700041) 2017; 7
Charette, AB (000498944300001.8) 2001; 58
Pellissier, H (WOS:000257619700001) 2008; 64
Phelan, JP (WOS:000436910300037) 2018; 140
Lin, K (WOS:000411034400002) 2017; 94
Guo, T (WOS:000451894400001) 2018; 360
Yan, M (WOS:000384952100001) 2016; 138
Liu, ZH (WOS:000418392400047) 2017; 19
Allouche, EMD (WOS:000451016200014) 2018; 54
Lang, SB (WOS:000445812900052) 2017; 56
Allouche, EMD (WOS:000462795800011) 2019; 10
Luo, WP (WOS:000487083200005) 2019; 361
Pantaine, LRE (WOS:000464247500082) 2019; 21
Milligan, JA (WOS:000449443100049) 2018; 20
Cartier, A (WOS:000458826800043) 2019; 58
Luo, J (WOS:000369774900048) 2016; 6
FAWZI, MM (WOS:A19667701900018) 1966; 31
Lecornué, F (WOS:000186180300019) 2003; 1
Sampson, PB (WOS:000347743700009) 2015; 58
Qian, DY (WOS:000348922100006) 2015; 44
References_xml – volume: 57
  start-page: 1543
  year: 2018
  publication-title: Angew. Chem. Int. Ed.
– volume: 49
  start-page: 2273
  year: 2016
  publication-title: Acc. Chem. Res.
– volume: 86
  start-page: 3170
  year: 1964
  publication-title: J. Am. Chem. Soc.
– volume: 1
  start-page: 3600
  year: 2003
  publication-title: Org. Biomol. Chem.
– volume: 44
  start-page: 677
  year: 2015
  publication-title: Chem. Soc. Rev.
– volume: 132
  start-page: 17894
  year: 2010
  publication-title: J. Am. Chem. Soc.
– start-page: 548
  year: 1973
  publication-title: J. Chem. Soc. Chem. Commun.
– volume: 69
  start-page: 6897
  year: 2004
  publication-title: J. Org. Chem.
– volume: 7
  start-page: 2563
  year: 2017
  publication-title: ACS Catal.
– volume: 20
  start-page: 6840
  year: 2018
  publication-title: Org. Lett.
– volume: 10
  start-page: 3802
  year: 2019
  publication-title: Chem. Sci.
– volume: 94
  start-page: 16
  year: 2017
  publication-title: Org. Synth.
– year: 1996
– volume: 6
  start-page: 873
  year: 2016
  publication-title: ACS Catal.
– volume: 64
  start-page: 7041
  year: 2008
  publication-title: Tetrahedron
– volume: 57
  start-page: 1855
  year: 2014
  publication-title: J. Med. Chem.
– volume: 46
  start-page: 979
  year: 2014
  publication-title: Synthesis
– volume: 361,
  start-page: 4215
  year: 2019
  publication-title: Adv. Synth. Catal.
– volume: 19
  start-page: 6646
  year: 2017
  publication-title: Org. Lett.
– volume: 1
  start-page: 1035
  year: 2014
  publication-title: Org. Chem. Front.
– volume: 31
  start-page: 1390
  year: 1966
  publication-title: J. Org. Chem.
– volume: 57
  start-page: 15430
  year: 2018
  publication-title: Angew. Chem. Int. Ed.
– volume: 54
  start-page: 13256
  year: 2018
  publication-title: Chem. Commun.
– volume: 140
  start-page: 8037
  year: 2018
  publication-title: J. Am. Chem. Soc.
– volume: 56
  start-page: 15073
  year: 2017
  publication-title: Angew. Chem. Int. Ed.
– volume: 7
  start-page: 1766
  year: 2017
  publication-title: ACS Catal.
– volume: 58
  start-page: 1789
  year: 2019
  publication-title: Angew. Chem. Int. Ed.
– volume: 103
  start-page: 977
  year: 2003
  publication-title: Chem. Rev.
– volume: 58
  start-page: 1
  year: 2001
  end-page: 395
  publication-title: Org. React.
– volume: 21
  start-page: 2317
  year: 2019
  publication-title: Org. Lett.
– volume: 59
  start-page: 8712
  year: 2016
  publication-title: J. Med. Chem.
– start-page: 3360
  year: 2005
  publication-title: Eur. J. Org. Chem.
– volume: 53
  start-page: 6986
  year: 2010
  publication-title: J. Med. Chem.
– volume: 58
  start-page: 130
  year: 2015
  publication-title: J. Med. Chem.
– volume: 138
  start-page: 12692
  year: 2016
  publication-title: J. Am. Chem. Soc.
– volume: 51
  start-page: 2821
  year: 2019
  publication-title: Synthesis
– volume: 360
  start-page: 4459
  year: 2018
  publication-title: Adv. Synth. Catal.
– ident: e_1_2_6_14_2
  doi: 10.1021/ja1084749
– volume: 58
  start-page: 1
  year: 2001
  ident: e_1_2_6_13_2
  publication-title: Org. React.
– ident: e_1_2_6_41_2
  doi: 10.1021/acscatal.6b03665
– ident: e_1_2_6_26_1
  doi: 10.1021/acscatal.7b00094
– ident: e_1_2_6_32_2
  doi: 10.1021/acs.orglett.8b02968
– ident: e_1_2_6_20_2
  doi: 10.1039/C39730000548
– ident: e_1_2_6_31_1
– ident: e_1_2_6_44_1
  doi: 10.1021/acscatal.5b02204
– ident: e_1_2_6_18_1
– ident: e_1_2_6_19_2
  doi: 10.1002/ejoc.200500143
– ident: e_1_2_6_16_2
  doi: 10.1039/C8SC05558K
– ident: e_1_2_6_35_1
  doi: 10.1021/jacs.6b08856
– ident: e_1_2_6_42_2
  doi: 10.1002/anie.201811858
– ident: e_1_2_6_24_2
  doi: 10.1039/C4QO00232F
– ident: e_1_2_6_37_1
– ident: e_1_2_6_4_2
  doi: 10.1021/cr010007e
– ident: e_1_2_6_39_2
  doi: 10.15227/orgsyn.094.0016
– ident: e_1_2_6_45_1
  doi: 10.1021/acs.accounts.6b00259
– ident: e_1_2_6_22_1
– ident: e_1_2_6_8_1
  doi: 10.1021/acs.jmedchem.6b00472
– ident: e_1_2_6_10_1
  doi: 10.1021/jm500537u
– ident: e_1_2_6_11_1
  doi: 10.1021/jm1006269
– ident: e_1_2_6_33_2
  doi: 10.1002/anie.201710707
– ident: e_1_2_6_9_1
  doi: 10.1021/jm4016894
– ident: e_1_2_6_43_2
  doi: 10.1002/anie.201709487
– ident: e_1_2_6_34_2
  doi: 10.1002/adsc.201900708
– ident: e_1_2_6_38_2
  doi: 10.1021/ja01069a054
– volume-title: The Chemistry of the Cyclopropyl Group.
  year: 1996
  ident: e_1_2_6_3_2
– ident: e_1_2_6_5_2
  doi: 10.1016/j.tet.2008.04.079
– ident: e_1_2_6_23_2
  doi: 10.1021/acs.orglett.7b03374
– ident: e_1_2_6_2_1
– ident: e_1_2_6_28_2
  doi: 10.1021/jacs.8b05243
– ident: e_1_2_6_27_1
– ident: e_1_2_6_40_2
  doi: 10.1021/acs.orglett.9b00602
– ident: e_1_2_6_6_2
  doi: 10.1055/s-0033-1340838
– ident: e_1_2_6_21_2
  doi: 10.1021/jo01343a018
– ident: e_1_2_6_25_2
  doi: 10.1002/anie.201808598
– ident: e_1_2_6_46_1
  doi: 10.1039/B307289B
– ident: e_1_2_6_29_2
  doi: 10.1002/adsc.201800761
– ident: e_1_2_6_15_1
– ident: e_1_2_6_30_2
  doi: 10.1055/s-0037-1611872
– ident: e_1_2_6_7_2
  doi: 10.1039/C4CS00304G
– ident: e_1_2_6_17_2
  doi: 10.1039/C8CC07060A
– ident: e_1_2_6_12_1
– ident: e_1_2_6_36_1
  doi: 10.1021/jo0401772
– year: 1996
  ident: 000498944300001.30
  publication-title: The Chemistry of the Cyclopropyl Group.
– volume: 44
  start-page: 677
  year: 2015
  ident: WOS:000348922100006
  article-title: Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox
  publication-title: CHEMICAL SOCIETY REVIEWS
  doi: 10.1039/c4cs00304g
– volume: 51
  start-page: 2821
  year: 2019
  ident: WOS:000479153600005
  article-title: New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-0037-1611872
– volume: 58
  start-page: 1789
  year: 2019
  ident: WOS:000458826800043
  article-title: Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201811858
– volume: 69
  start-page: 6897
  year: 2004
  ident: WOS:000224143000048
  article-title: Enantioselective alkylation of β-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo0401772
– volume: 46
  start-page: 979
  year: 2014
  ident: WOS:000336838900001
  article-title: Asymmetric Cyclopropanation Reactions
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-0033-1340838
– volume: 21
  start-page: 2317
  year: 2019
  ident: WOS:000464247500082
  article-title: Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.9b00602
– volume: 58
  start-page: 147
  year: 2015
  ident: WOS:000347743700009
  article-title: The Discovery of Polo-Like Kinase 4 Inhibitors: Identification of (1R,2S)-2-(3((E)-4-(((cis)-2,6-Dimethylmorpholino)methyl)styryl)-1H-indazol-6-yl)-5′-methoxyspiro[cyclopropane-1,3′-indolin]-2′-one (CFI-400945) as a Potent, Orally Active Antitumor Agent
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm5005336
– volume: 86
  start-page: 3170
  year: 1964
  ident: WOS:A19643125B00017
  article-title: PENTACOORDINATE SILICON DERIVATIVES .2. SALTS OF BIS(OMICRON-ARYLENEDIOXY)ORGANOSILICONIC ACIDS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
– volume: 140
  start-page: 8037
  year: 2018
  ident: WOS:000436910300037
  article-title: Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.8b05243
– volume: 94
  start-page: 16
  year: 2017
  ident: WOS:000411034400002
  article-title: Preparation of Diisopropylammonium Bis(catecholato)cyclohexylsilicate
  publication-title: ORGANIC SYNTHESES
  doi: 10.15227/orgsyn.094.0016
– volume: 361
  start-page: 4215
  year: 2019
  ident: WOS:000487083200005
  article-title: Photoredox-Catalyzed Cyclopropanation of 1,1-Disubstituted Alkenes via Radical-Polar Crossover Process
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201900708
– volume: 57
  start-page: 1855
  year: 2014
  ident: WOS:000333005800017
  article-title: Discovery and Preclinical Characterization of the Cyclopropylindolobenzazepine BMS-791325, A Potent Allosteric Inhibitor of the Hepatitis C Virus NS5B Polymerase
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm4016894
– volume: 7
  start-page: 1766
  year: 2017
  ident: WOS:000395726500032
  article-title: Mild, Redox-Neutral Alkylation of !mines Enabled by an Organic Photocatalyst
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.6b03665
– volume: 19
  start-page: 6646
  year: 2017
  ident: WOS:000418392400047
  article-title: Silver-Catalyzed Cyclopropanation of Alkenes Using N-Nosylhydrazones as Diazo Surrogates
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.7b03374
– volume: 54
  start-page: 13256
  year: 2018
  ident: WOS:000451016200014
  article-title: Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c8cc07060a
– volume: 56
  start-page: 15073
  year: 2017
  ident: WOS:000445812900052
  article-title: Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201709487
– volume: 2005
  start-page: 3360
  year: 2005
  ident: WOS:000231025500024
  article-title: Preparation of conformationally constrained α2 antagonists:: The bicyclo[3.1.0]hexane approach
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.200500143
– volume: 7
  start-page: 2563
  year: 2017
  ident: WOS:000398986700041
  article-title: Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.7b00094
– volume: 103
  start-page: 977
  year: 2003
  ident: WOS:000182150900003
  article-title: Stereoselective cyclopropanation reactions
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr010007e
– volume: 20
  start-page: 6840
  year: 2018
  ident: WOS:000449443100049
  article-title: Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.8b02968
– volume: 360
  start-page: 4459
  year: 2018
  ident: WOS:000451894400001
  article-title: Visible-Light-Promoted Redox-Neutral Cyclopropanation Reactions of α-Substituted Vinylphosphonates and Other Michael Acceptors with Chloromethyl Silicate as Methylene Transfer Reagent
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201800761
– volume: 58
  start-page: 1
  year: 2001
  ident: 000498944300001.8
  article-title: Simmons-Smith cyclopropanation reaction
  publication-title: Org. React
– volume: 10
  start-page: 3802
  year: 2019
  ident: WOS:000462795800011
  article-title: Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c8sc05558k
– start-page: 548
  year: 1973
  ident: WOS:A1973Q357600036
  article-title: INTRAMOLECULAR KETO-CARBENOID ADDITION TO DOUBLE-BONDS - STEREOCHEMISTRY OF CATALYTIC REDUCTION OF DELTA9(11)-GIBBENES AND RELATED COMPOUNDS
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
– volume: 1
  start-page: 3600
  year: 2003
  ident: WOS:000186180300019
  article-title: Construction of medium-ring oxacycloalkenones.: Extension towards benzo-fused cyclic ethers
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/b307289b
– volume: 64
  start-page: 7041
  year: 2008
  ident: WOS:000257619700001
  article-title: Recent developments in asymmetric cyclopropanation
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2008.04.079
– volume: 53
  start-page: 6986
  year: 2010
  ident: WOS:000282544800016
  article-title: Rigid Analogues of the α2-Adrenergic Blocker Atipamezole: Small Changes, Big Consequences
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm1006269
– volume: 138
  start-page: 12692
  year: 2016
  ident: WOS:000384952100001
  article-title: Radicals: Reactive Intermediates with Translational Potential
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b08856
– volume: 132
  start-page: 17894
  year: 2010
  ident: WOS:000285429800042
  article-title: Scope and Limitations of Cyclopropanations with Sulfur Ylides
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja1084749
– volume: 31
  start-page: 1390
  year: 1966
  ident: WOS:A19667701900018
  article-title: INTRAMOLECULAR REACTIONS OF OLEFINIC DIAZO KETONES
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
– volume: 1
  start-page: 1035
  year: 2014
  ident: WOS:000364430400002
  article-title: A sidearm-assisted phosphine for catalytic ylide intramolecular cyclopropanation
  publication-title: ORGANIC CHEMISTRY FRONTIERS
  doi: 10.1039/c4qo00232f
– volume: 6
  start-page: 873
  year: 2016
  ident: WOS:000369774900048
  article-title: Donor-Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis:Photoredox/Ni Dual Catalytic C(sp3)-C(sp2) Cross-Coupling
  publication-title: ACS CATALYSIS
  doi: 10.1021/acscatal.5b02204
– volume: 49
  start-page: 2273
  year: 2016
  ident: WOS:000385908100023
  article-title: Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/acs.accounts.6b00259
– volume: 59
  start-page: 8712
  year: 2016
  ident: WOS:000385607100004
  article-title: The "Cyclopropyl Fragment" is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/acs.jmedchem.6b00472
– volume: 57
  start-page: 15430
  year: 2018
  ident: WOS:000453344500021
  article-title: Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201808598
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Snippet Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the...
Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the...
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SubjectTerms Alkenes
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Crossovers
Cyclization
Cyclopropanes
Embedded systems
Organic compounds
Photoredox Catalysis
Physical Sciences
Radical/Polar Crossover
Radicals
Science & Technology
Substitution reactions
Title Radical‐Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.201901051
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https://www.proquest.com/docview/2334656940
https://www.proquest.com/docview/2537638973
https://pubmed.ncbi.nlm.nih.gov/PMC8172062
Volume 362
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