Anti-Markovnikov Hydroarylation of Unactivated Olefins via Pyridyl Radical Intermediates

被引：98

作者：

Boyington, Allyson J. ^{[1
]}

Riu, Martin-Louis Y. ^{[1
]}

Jui, Nathan T. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Winship Canc Inst, 1515 Pierce Dr, Atlanta, GA 30322 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 19期

关键词：

C-H FUNCTIONALIZATION; NITROGEN-HETEROCYCLES; BOND ACTIVATION; ALKYLATION; CATALYSIS; PHOTOCATALYSIS; GENERATION; ARYLATION; ALKENES; ACCESS;

D O I：

10.1021/jacs.7b03262

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intermolecular alkylation of pyridine units with simple alkenes has been achieved via a photoredox radical mechanism. This process occurs with complete regiocontrol, where single-electron reduction of halogenated pyridines regiospecifically yields the corresponding radicals in a programmed fashion, and radical addition to alkene substrates occurs with exclusive antiMarkovnikov selectivity. This system is mild, tolerant of many functional groups, and effective for the preparation of a wide range of complex alkylpyridines.

引用

页码：6582 / 6585

页数：4

共 30 条

[1] Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges
Andreatta, Jeremy R.
McKeown, Bradley A.
Gunnoe, T. Brent
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 305 - 315
[2] HETEROGENEOUS AND HOMOGENEOUS ELECTRON TRANSFERS TO AROMATIC HALIDES - ELECTROCHEMICAL REDOX CATALYSIS STUDY IN THE HALOBENZENE AND HALOPYRIDINE SERIES
ANDRIEUX, CP
BLOCMAN, C
DUMASBOUCHIAT, JM
SAVEANT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (13) : 3431 - 3441
[3] Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates
Arora, Amandeep
Weaver, Jimmie D.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2273 - 2283
[4] Photocatalytic Generation of 2-Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C-H Functionalization
Arora, Amandeep
Weaver, Jimmie D.
[J]. ORGANIC LETTERS, 2016, 18 (16) : 3996 - 3999
[5] A mild catalytic system for radical conjugate addition of nitrogen heterocycles
Aycock, R. A.
Wang, H.
Jui, N. T.
[J]. CHEMICAL SCIENCE, 2017, 8 (04) : 3121 - 3125
[6] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS
BUNNETT, JF
ZAHLER, RE
[J]. CHEMICAL REVIEWS, 1951, 49 (02) : 273 - 412
[7] Fragmentation of aryl halide π anion radicals.: Bending of the cleaving bond and activation vs driving force relationships
Costentin, C
Robert, M
Savéant, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) : 16051 - 16057
[8] Branch Selective Mural-type Alkene Hydroarylation Reactions
Crisenza, Giacomo E. M.
Bower, John F.
[J]. CHEMISTRY LETTERS, 2016, 45 (01) : 2 - 9
[9] A highly reducing metal-free photoredox catalyst: design and application in radical dehalogenations
Discekici, Emre H.
Treat, Nicolas J.
Poelma, Saemi O.
Mattson, Kaila M.
Hudson, Zachary M.
Luo, Yingdong
Hawker, Craig J.
de Alaniz, Javier Read
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (58) : 11705 - 11708
[10] Enemrke R. J., 2001, J CHEM SOC P2, V9, P1620

← 1 2 3 →