Direct Cross-Coupling of Allylic C(sp3)-H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis

被引:119
作者
Huang, Long [1 ]
Rueping, Magnus [1 ,2 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
基金
欧洲研究理事会;
关键词
alkenes; allylic compounds; C-H activation; nickel; photocatalysis; PHOTOREDOX/NICKEL DUAL CATALYSIS; ROOM-TEMPERATURE; OXIDATIVE ADDITION; HALIDES; PALLADIUM; ACETATES; BROMIDES; DERIVATIVES; 9-MESITYL-10-METHYLACRIDINIUM; ARYLATION;
D O I
10.1002/anie.201805118
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient protocol for the direct allylic C(sp(3))-H bond activation of unactivated tri- and tetrasubstituted alkenes and their functionalization with aryl- and vinylbromides by nickel and visible-light photocatalysis has been developed. The method allows C(sp(2))-C(sp(3)) formation under mild reaction conditions with good functional-group tolerance and excellent regioselectivity.
引用
收藏
页码:10333 / 10337
页数:5
相关论文
共 64 条
[1]   Selective Cross-Coupling of Organic Halides with Allylic Acetates [J].
Anka-Lufford, Lukiana L. ;
Prinsell, Michael R. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :9989-10000
[2]   Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships [J].
Bajo, Sonia ;
Laidlaw, Gillian ;
Kennedy, Alan R. ;
Sproules, Stephen ;
Nelson, David J. .
ORGANOMETALLICS, 2017, 36 (08) :1662-1672
[3]   Charge shift and triplet state formation in the 9-mesityl-10-methylacridinium cation [J].
Benniston, AC ;
Harriman, A ;
Li, PY ;
Rostron, JP ;
van Ramesdonk, HJ ;
Groeneveld, MM ;
Zhang, H ;
Verhoeven, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16054-16064
[4]   RADICAL IONS IN PHOTOCHEMISTRY .15. THE PHOTOSUBSTITUTION REACTION BETWEEN DICYANOBENZENES AND ALKYL OLEFINS [J].
BORG, RM ;
ARNOLD, DR ;
CAMERON, TS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (09) :1785-1802
[5]   Aryl amination using ligand-free Ni(II) salts and photoredox catalysis [J].
Corcoran, Emily B. ;
Pirnot, Michael T. ;
Lin, Shishi ;
Dreher, Spencer D. ;
DiRocco, Daniel A. ;
Davies, Ian W. ;
Buchwald, Stephen L. ;
MacMillan, David W. C. .
SCIENCE, 2016, 353 (6296) :279-283
[6]   Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates [J].
Cui, Xiaozhan ;
Wang, Shulin ;
Zhang, Yuwei ;
Deng, Wei ;
Qian, Qun ;
Gong, Hegui .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (19) :3094-3097
[7]   The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis [J].
Cuthbertson, James D. ;
MacMillan, David W. C. .
NATURE, 2015, 519 (7541) :74-77
[8]   PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ARYLSTANNANES AND VINYLSTANNANES [J].
DELVALLE, L ;
STILLE, JK ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3019-3023
[9]   Photoinduced Nickel-Catalyzed Chemo- and Regioselective Hydroalkylation of Internal Alkynes with Ether and Amide α-Hetero C(sp3)-H Bonds [J].
Deng, Hong-Ping ;
Fan, Xuan-Zi ;
Chen, Zhi-Hui ;
Xu, Qing-Hua ;
Wu, Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (38) :13579-13584
[10]   Palladium(0) Nanoparticle Catalyzed Cross-Coupling of Allyl Acetates and Aryl and Vinyl Siloxanes [J].
Dey, Raju ;
Chattopadhyay, Kalicharan ;
Ranu, Brinclaban C. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9461-9464