Visible-light-driven three-component reductive 1,2-diarylation of alkenes

被引:13
作者
Wang, Tao [1 ,2 ]
Yu, Weijie [1 ,2 ]
Lan, Jinping [1 ,2 ]
Wang, Hongyu [3 ]
Jiang, Zhou [1 ,2 ]
Li, Yang [3 ]
Fu, Junkai [3 ]
机构
[1] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Key Lab Fluorine & Silicon Energy Mat, Nanchang 330022, Jiangxi, Peoples R China
[2] Jiangxi Normal Univ, Jiangxi Prov Key Lab Chem Biol, Nanchang 330022, Jiangxi, Peoples R China
[3] Northeast Normal Univ, Dept Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Jilin, Peoples R China
来源
CHEM CATALYSIS | 2023年 / 3卷 / 05期
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
ALPHA-AMINOALKYL RADICALS; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; OXIDATIVE ADDITION; UNACTIVATED ALKYL; DIRECT ARYLATION; ARYL RADICALS; DIARYLATION; DICARBOFUNCTIONALIZATION; DIFUNCTIONALIZATION;
D O I
10.1016/j.checat.2023.100619
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The intermolecular alkene 1,2-diary lation provides straightforward access to polyarylalkanes but suffers from substrate limitation, requiring directing auxiliaries or prefunctionalized aryl compo-nents. Herein, we report the development of a photocatalytic strat-egy that enables a three-component 1,2-diarylation of alkenes under mild reductive conditions using simple tertiary alkylamine as the terminal reductant. Readily accessible aryl iodides and cyanides serve as the C(sp2) electrophiles to simultaneously install two different aryl moieties across the olefins with high regioselectivity. This protocol exhibits a broad substrate scope for all of aryl, hetero-atom-substituted, and even unactivated alkenes and can be easily scaled up to the gram-scale. Mechanistic studies reveal a halogen -atom transfer (XAT) of aryl iodides to transient aryl radicals while a single-electron transfer (SET) of aryl cyanides to persistent aryl radical anions, both allowing for a regiocontrollable radical relay sequence.
引用
收藏
页数:16
相关论文
共 79 条
[1]   Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes [J].
Anthony, David ;
Lin, Qiao ;
Baudet, Judith ;
Diao, Tianning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3198-3202
[2]   Iron Catalyzed Oxidative Hydroarylation, Methylarylation, and Diarylation of Vinylarenes to Generate Unsymmetrical 1,1-Diarylalkanes [J].
Babu, Kaki Raveendra ;
Chen, Shaowei ;
Li, Yajun ;
Bao, Hongli .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (05) :1160-1164
[3]   Aryldiazonium Salts in Photoredox Catalysis - Recent Trends [J].
Babu, Sakamuri Sarath ;
Muthuraja, P. ;
Yadav, Pooja ;
Gopinath, Purushothaman .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) :1782-1809
[4]   Tuning Redox States of Phenalenyl-Based Molecules by Consecutive Reduction toward Transition Metal-Free Heck-Type C-C Cross-Coupling [J].
Banik, Ananya ;
Mandal, Swadhin K. .
ACS CATALYSIS, 2022, 12 (09) :5000-5012
[5]   Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts [J].
Basnet, Prakash ;
Shekhar, K. C. ;
Dhungana, Roshan K. ;
Shrestha, Bijay ;
Boyle, Timothy J. ;
Giri, Ramesh .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (46) :15586-15590
[6]   Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis [J].
Beatty, Joel W. ;
Stephenson, Corey R. J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1474-1484
[7]   DYNAMIC ETA-1-BENZYLBIS(TRIETHYLPHOSPHINE) AND ETA-3-BENZYLBIS(TRIETHYLPHOSPHINE)PALLADIUM(II) CATIONS - MECHANISMS OF INTERCONVERSION [J].
BECKER, Y ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (03) :845-850
[8]   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
[9]   Catalytic Strategy for Regioselective Arylethylamine Synthesis [J].
Boyington, Allyson J. ;
Seath, Ciaran P. ;
Zearfoss, Avery M. ;
Xu, Zihao ;
Jui, Nathan T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (09) :4147-4153
[10]   A NEW PALLADIUM CATALYZED SYNTHESIS OF CIS,EXO-2,3-DIARYLSUBSTITUTED BICYCLO[2.2.1]HEPTANES OR BICYCLO[2.2.1]HEPT-2-ENES [J].
CATELLANI, M ;
CHIUSOLI, GP ;
CONCARI, S .
TETRAHEDRON, 1989, 45 (16) :5263-5268