Synthesis of Tetrasubstituted Allenes via Visible-Light-Promoted Radical 1,3-Difunctionalization of Alkynyl Diazo Compounds

Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubst...

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Published inOrganic letters Vol. 24; no. 22; pp. 3976 - 3981
Main Authors Li, Weiyu, Zhou, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.06.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
diazo compounds
light
nitrogen
photocatalysts
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
SPECTROSCOPY
PROPARGYL
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Abstract Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO2X (X = SeR′, SR′, and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
AbstractList Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO2X (X = SeR′, SR′, and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO X (X = SeR', SR', and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO₂X (X = SeR′, SR′, and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO2X (X = SeR', SR', and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO2X (X = SeR', SR', and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
Author Li, Weiyu
Zhou, Lei
AuthorAffiliation School of Chemistry
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Cites_doi 10.1016/S0040-4039(00)00067-8
10.1021/jo001483s
10.1021/jacs.7b09622
10.1002/anie.202013022
10.1021/ja00093a017
10.1021/ja01022a029
10.1021/jacs.6b07444
10.1038/s41467-020-20740-w
10.1002/anie.201511139
10.1002/anie.200300628
10.1039/D1GC02036F
10.1002/anie.202106145
10.1021/jacs.0c06177
10.1021/acs.orglett.0c02638
10.1002/anie.201803668
10.1039/C8CC03760D
10.1021/acs.joc.5b01684
10.1021/ja110898s
10.1021/ar500365v
10.1021/cs401007m
10.1021/jacs.1c03435
10.1002/cjoc.201900277
10.1021/ja901606a
10.1021/jacs.6b11937
10.1002/chem.201701462
10.1021/cr020024j
10.1021/acs.accounts.9b00023
10.1021/jo302704g
10.1021/acs.orglett.9b02139
10.1002/anie.201813184
10.1002/anie.202012027
10.1021/jo026579w
10.1039/a800077h
10.1038/s41467-017-00251-x
10.1002/adsc.201600986
10.1016/S0040-4039(00)01453-2
10.1002/9783527619573
10.1021/ja901528b
10.1039/C0CC05640E
10.1002/anie.200704221
10.1039/c0cc05640e
10.1039/d1gc02036f
10.1039/c8cc03760d
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References ref17/cit17b
ref15/cit15a
ref17/cit17a
ref10/cit10d
Li W. (ref16/cit16a) 2021; 3
ref9/cit9b
ref10/cit10e
Schuster H. F. (ref1/cit1b1) 1984
ref9/cit9a
ref11/cit11
ref15/cit15b
ref13/cit13a
ref8/cit8a
ref13/cit13b
ref10/cit10a
ref10/cit10b
ref8/cit8b
ref10/cit10c
ref12/cit12b
ref12/cit12a
ref2/cit2
ref1/cit1b
ref5/cit5b
ref5/cit5c
ref18/cit18d
ref5/cit5a
ref18/cit18b
ref4/cit4a
ref16/cit16b
ref18/cit18c
ref4/cit4b
ref18/cit18a
ref14/cit14a
ref14/cit14c
ref14/cit14b
ref3/cit3b
ref3/cit3c
ref3/cit3a
Krause N. (ref1/cit1a) 2004
ref6/cit6a
ref6/cit6b
ref7/cit7
Liu, HJ (WOS:000266484900004) 2009; 131
Hansmann, MM (WOS:000415028200017) 2017; 139
Davies, HML (WOS:000090123600001) 2000; 41
Neff, RK (WOS:000331164000019) 2014; 4
Zeng, YH (WOS:000580559000025) 2020; 142
Fu, L (WOS:000500531200001) 2020; 38
Yang, Y (WOS:000404854700002) 2017; 23
NORO, M (WOS:A1994NX54800017) 1994; 116
Wang, B (WOS:000584080700001) 2021; 60
Melikyan, GG (WOS:000353429400017) 2015; 48
Jammi, S (WOS:000315254100029) 2013; 78
Seburg, RA (WOS:000267633300061) 2009; 131
Yu, SC (WOS:000289899600003) 2011; 47
Yang, Z (WOS:000361866700032) 2015; 80
Kaiser, RI (WOS:000076353800012) 1998; 109
Yu, SF (WOS:000476957200076) 2019; 21
Schuster, H. F. (000810536100001.1) 1984
Pei, C (WOS:000574921100047) 2020; 22
Knezz, SN (WOS:000384518400042) 2016; 138
Guisán-Ceinos, M (WOS:000439702200010) 2018; 54
Adam, W (WOS:000180834600044) 2003; 68
Dong, XY (WOS:000592473500001) 2021; 60
Yang, LL (WOS:000648704100015) 2021; 143
FANTAZIER, RM (WOS:A1968B835100029) 1968; 90
Wang, F (WOS:000434350400029) 2018; 57
Li, W. (000810536100001.33) 1000; 2021
Kessler, SN (WOS:000371521000035) 2016; 55
Xu, B (WOS:000252652200012) 2008; 47
Huang, X (WOS:000469304100018) 2019; 52
Zhang, G (WOS:000616943800002) 2021; 12
Hoffmann-Röder, A (WOS:000220120000003) 2004; 43
Jiang, Y (WOS:000393848400049) 2017; 139
Wei, YL (WOS:000678178800001) 2021; 60
Tomida, Y (WOS:000288889900016) 2011; 133
Zhang, KF (WOS:000463739900049) 2019; 58
Tata, RR (WOS:000398534000017) 2017; 359
Shimizu, T (WOS:000167403900035) 2001; 66
Li, WY (WOS:000686725100001) 2021; 23
Qian, DY (WOS:000411024900003) 2017; 8
References_xml – ident: ref18/cit18a
  doi: 10.1016/S0040-4039(00)00067-8
– ident: ref18/cit18b
  doi: 10.1021/jo001483s
– ident: ref8/cit8b
  doi: 10.1021/jacs.7b09622
– ident: ref10/cit10e
  doi: 10.1002/anie.202013022
– ident: ref13/cit13b
  doi: 10.1021/ja00093a017
– ident: ref9/cit9a
  doi: 10.1021/ja01022a029
– ident: ref12/cit12b
  doi: 10.1021/jacs.6b07444
– ident: ref17/cit17a
  doi: 10.1038/s41467-020-20740-w
– ident: ref5/cit5c
  doi: 10.1002/anie.201511139
– ident: ref2/cit2
  doi: 10.1002/anie.200300628
– ident: ref16/cit16b
  doi: 10.1039/D1GC02036F
– ident: ref7/cit7
  doi: 10.1002/anie.202106145
– ident: ref10/cit10d
  doi: 10.1021/jacs.0c06177
– ident: ref17/cit17b
  doi: 10.1021/acs.orglett.0c02638
– ident: ref10/cit10b
  doi: 10.1002/anie.201803668
– ident: ref5/cit5a
  doi: 10.1039/C8CC03760D
– ident: ref18/cit18c
  doi: 10.1021/acs.joc.5b01684
– ident: ref6/cit6a
  doi: 10.1021/ja110898s
– ident: ref8/cit8a
  doi: 10.1021/ar500365v
– ident: ref3/cit3b
  doi: 10.1021/cs401007m
– ident: ref14/cit14a
  doi: 10.1021/jacs.1c03435
– ident: ref10/cit10a
  doi: 10.1002/cjoc.201900277
– ident: ref12/cit12a
  doi: 10.1021/ja901606a
– ident: ref15/cit15a
  doi: 10.1021/jacs.6b11937
– ident: ref15/cit15b
  doi: 10.1002/chem.201701462
– ident: ref1/cit1b
  doi: 10.1021/cr020024j
– ident: ref3/cit3a
  doi: 10.1021/acs.accounts.9b00023
– volume-title: Allenes in Organic Synthesis
  year: 1984
  ident: ref1/cit1b1
– volume: 3
  start-page: 794
  year: 2021
  ident: ref16/cit16a
  publication-title: CCS Chem.
– ident: ref9/cit9b
  doi: 10.1021/jo302704g
– ident: ref14/cit14c
  doi: 10.1021/acs.orglett.9b02139
– ident: ref10/cit10c
  doi: 10.1002/anie.201813184
– ident: ref6/cit6b
  doi: 10.1002/anie.202012027
– ident: ref11/cit11
  doi: 10.1021/jo026579w
– ident: ref13/cit13a
  doi: 10.1039/a800077h
– ident: ref5/cit5b
  doi: 10.1038/s41467-017-00251-x
– ident: ref18/cit18d
  doi: 10.1002/adsc.201600986
– ident: ref14/cit14b
  doi: 10.1016/S0040-4039(00)01453-2
– volume-title: Modern Allene Chemistry
  year: 2004
  ident: ref1/cit1a
  doi: 10.1002/9783527619573
– ident: ref4/cit4b
  doi: 10.1021/ja901528b
– ident: ref3/cit3c
  doi: 10.1039/C0CC05640E
– ident: ref4/cit4a
  doi: 10.1002/anie.200704221
– volume: 90
  start-page: 5490
  year: 1968
  ident: WOS:A1968B835100029
  article-title: REDUCTION OF PROPARGYLIC CHLORIDES WITH TRI-N-BUTYLTIN HYDRIDE . AMBIDENT BEHAVIOR OF PROPARGYLIC RADICALS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
– volume: 68
  start-page: 1007
  year: 2003
  ident: WOS:000180834600044
  article-title: Spin delocalization by triple-bonded functionalities in propargyl and heteropropargyl radicals, assessed from the EPR-spectral D parameter of 1,3-cyclopentanediyl triplet diradicals
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo026579w
– volume: 139
  start-page: 1998
  year: 2017
  ident: WOS:000393848400049
  article-title: Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b11937
– volume: 58
  start-page: 5069
  year: 2019
  ident: WOS:000463739900049
  article-title: Nickel-Catalyzed Carbofluoroalkylation of 1,3-Enynes to Access Structurally Diverse Fluoroalkylated Allenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201813184
– volume: 4
  start-page: 519
  year: 2014
  ident: WOS:000331164000019
  article-title: Recent Advances in the Catalytic Syntheses of Allenes: A Critical Assessment
  publication-title: ACS CATALYSIS
  doi: 10.1021/cs401007m
– volume: 133
  start-page: 3744
  year: 2011
  ident: WOS:000288889900016
  article-title: Asymmetric Carbolithiation of Conjugated Enynes: A Flow Microreactor Enables the Use of Configurationally Unstable Intermediates before They Epimerize
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja110898s
– volume: 38
  start-page: 91
  year: 2020
  ident: WOS:000500531200001
  article-title: Recent Advances and Perspectives in Transition Metal-Catalyzed 1,4-Functionalizations of Unactivated 1,3-Enynes for the Synthesis of Allenes
  publication-title: CHINESE JOURNAL OF CHEMISTRY
  doi: 10.1002/cjoc.201900277
– volume: 60
  start-page: 20215
  year: 2021
  ident: WOS:000678178800001
  article-title: Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C-C Bonds
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.202106145
– volume: 131
  start-page: 7212
  year: 2009
  ident: WOS:000266484900004
  article-title: Enantioselective Synthesis of Chiral Allenoates by Guanidine-Catalyzed Isomerization of 3-Alkynoates
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja901528b
– volume: 138
  start-page: 12596
  year: 2016
  ident: WOS:000384518400042
  article-title: Spectroscopy and Photochemistry of Triplet 1,3-Dimethylpropynylidene (MeC3Me)
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.6b07444
– volume: 131
  start-page: 9442
  year: 2009
  ident: WOS:000267633300061
  article-title: Structure of Triplet Propynylidene (HCCCH) as Probed by IR, UV/vis, and EPR Spectroscopy of Isotopomers
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja901606a
– volume: 142
  start-page: 18014
  year: 2020
  ident: WOS:000580559000025
  article-title: Copper-Catalyzed Enantioselective Radical 1,4-Difunctionalization of 1,3-Enynes
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.0c06177
– volume: 359
  start-page: 1232
  year: 2017
  ident: WOS:000398534000017
  article-title: Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201600986
– volume: 109
  start-page: 183
  year: 1998
  ident: WOS:000076353800012
  article-title: Combined crossed molecular beams and ab initio investigation of the formation of carbon-bearing molecules in the interstellar medium via neutral-neutral reactions
  publication-title: FARADAY DISCUSSIONS
– volume: 47
  start-page: 5384
  year: 2011
  ident: WOS:000289899600003
  article-title: How easy are the syntheses of allenes?
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c0cc05640e
– volume: 48
  start-page: 1065
  year: 2015
  ident: WOS:000353429400017
  article-title: Propargyl Radical Chemistry: Renaissance Instigated by Metal Coordination
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar500365v
– volume: 2021
  start-page: 794
  year: 1000
  ident: 000810536100001.33
  article-title: External Photocatalyst-free, Visible Light-Promoted 1,3-Addition of Perfluor- oalkyl Iodides to Vinyldiazoacetates
  publication-title: CCS Chem.
– volume: 60
  start-page: 217
  year: 2021
  ident: WOS:000584080700001
  article-title: Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.202012027
– volume: 43
  start-page: 1196
  year: 2004
  ident: WOS:000220120000003
  article-title: Synthesis and properties of allenic natural products and pharmaceuticals
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200300628
– volume: 12
  start-page: ARTN 728
  year: 2021
  ident: WOS:000616943800002
  article-title: Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from sp2-carbon
  publication-title: NATURE COMMUNICATIONS
  doi: 10.1038/s41467-020-20740-w
– volume: 80
  start-page: 9224
  year: 2015
  ident: WOS:000361866700032
  article-title: Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/acs.joc.5b01684
– volume: 52
  start-page: 1301
  year: 2019
  ident: WOS:000469304100018
  article-title: Alienation of Terminal Alkynes with Aldehydes and Ketones
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/acs.accounts.9b00023
– volume: 21
  start-page: 5737
  year: 2019
  ident: WOS:000476957200076
  article-title: Asymmetric Multicomponent Reactions for Efficient Construction of Homopropargyl Amine Carboxylic Esters
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.9b02139
– volume: 23
  start-page: 9009
  year: 2017
  ident: WOS:000404854700002
  article-title: Alkynyl N-Nosylhydrazones: Easy Decomposition to Alknynl Diazomethanes and Application in Allene Synthesis
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201701462
– volume: 66
  start-page: 1787
  year: 2001
  ident: WOS:000167403900035
  article-title: Synthesis and reactivity of allenes substituted by selenenyl groups at 1-and 3-positions
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
– volume: 41
  start-page: 8189
  year: 2000
  ident: WOS:000090123600001
  article-title: Asymmetric synthesis of 1-alkynylcyclopropane-1-carboxylates
  publication-title: TETRAHEDRON LETTERS
– volume: 116
  start-page: 6179
  year: 1994
  ident: WOS:A1994NX54800017
  article-title: CARBENE-CARBENE INTERCONVERSION BETWEEN 1-PHENYL-2-PROPYNYLIDENE AND 3-PHENYL-2-PROPYNYLIDENE
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
– volume: 143
  start-page: 6401
  year: 2021
  ident: WOS:000648704100015
  article-title: Enantioselective Insertion of Alkynyl Carbenes into Si-H Bonds: An Efficient Access to Chiral Propargylsilanes and Allenylsilanes
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.1c03435
– volume: 22
  start-page: 7300
  year: 2020
  ident: WOS:000574921100047
  article-title: Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.0c02638
– volume: 78
  start-page: 1589
  year: 2013
  ident: WOS:000315254100029
  article-title: Theoretical Support for the Involvement of a Radical Pathway in the Formation of Allenylzincs from Propargyl Iodides and Dialkylzincs: Influence of Zinc Coordination
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo302704g
– volume: 23
  start-page: 6652
  year: 2021
  ident: WOS:000686725100001
  article-title: Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/d1gc02036f
– volume: 60
  start-page: 2160
  year: 2021
  ident: WOS:000592473500001
  article-title: Copper-Catalyzed Asymmetric Coupling of Allenyl Radicals with Terminal Alkynes to Access Tetrasubstituted Allenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.202013022
– year: 1984
  ident: 000810536100001.1
  publication-title: Allenes in Organic Synthesis
– volume: 54
  start-page: 8343
  year: 2018
  ident: WOS:000439702200010
  article-title: Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c8cc03760d
– volume: 8
  start-page: ARTN 567
  year: 2017
  ident: WOS:000411024900003
  article-title: Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols
  publication-title: NATURE COMMUNICATIONS
  doi: 10.1038/s41467-017-00251-x
– volume: 57
  start-page: 7140
  year: 2018
  ident: WOS:000434350400029
  article-title: Divergent Synthesis of CF3-Substituted Allenyl Nitriles by Ligand-Controlled Radical 1,2-and 1,4-Addition to 1,3-Enynes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201803668
– volume: 47
  start-page: 689
  year: 2008
  ident: WOS:000252652200012
  article-title: Thermodynamically favored aldol reaction of propargyl or allenyl esters: Regioselective synthesis of carbinol allenoates
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200704221
– volume: 139
  start-page: 15620
  year: 2017
  ident: WOS:000415028200017
  article-title: Crystalline Monomeric Allenyl/Propargyl Radical
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/jacs.7b09622
– volume: 55
  start-page: 3734
  year: 2016
  ident: WOS:000371521000035
  article-title: Iron-catalyzed Cross-Coupling of Propargyl Carboxylates and Grignard Reagents: Synthesis of Substituted Allenes
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201511139
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Snippet Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical...
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SubjectTerms Chemistry
Chemistry, Organic
diazo compounds
light
nitrogen
photocatalysts
Physical Sciences
Science & Technology
Title Synthesis of Tetrasubstituted Allenes via Visible-Light-Promoted Radical 1,3-Difunctionalization of Alkynyl Diazo Compounds
URI http://dx.doi.org/10.1021/acs.orglett.2c01366
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https://www.ncbi.nlm.nih.gov/pubmed/35622019
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