Dual Cobalt and Photoredox Catalysis Enabled Redox-Neutral Annulation of 2-Propynolphenols

被引：21

作者：

Zhu, Yao ^{[1
]}

He, Yong-Qin ^{[2
]}

Tian, Wan-Fa ^{[1
]}

Wang, Mei ^{[1
]}

Zhou, Zhao-Zhao ^{[3
]}

Song, Xian-Rong ^{[1
]}

Ding, Hai-Xin ^{[1
]}

Xiao, Qiang ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Inst Organ Chem, Key Lab Organ Chem, Nanchang 330013, Jiangxi, Peoples R China

[2] Nanchang Univ, Sch Pharmaceut Sci, Nanchang 330006, Jiangxi, Peoples R China

[3] Nanchang Normal Univ, Dept Chem, Nanchang, Jiangxi, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 13期

基金：

中国国家自然科学基金;

关键词：

Photoredox catalysis; cobalt; hydrogen atom transfer (HAT); redox-neutral; 2-propynolphenols; BIOACTIVE BENZOFURAN DERIVATIVES; UNACTIVATED OLEFINS; ALKENES; HYDROAMINATION; CYCLIZATION; FE; CO; HYDROALKOXYLATION; HYDROGENATION; HETEROCYCLES;

D O I：

10.1002/adsc.202100221

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A hydroxyl-assisted, organophotoredox/cobalt dual catalyzed annulation of 2-propynolphenols to form 2-hydroxymethyl-benzo[b]furans was developed by employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as photosensitizer and CoCl2(PPh3)(2)/5,5 '-dimethyl-2,2 '-bipyridine as cobalt catalytic precursor. Various substrates and functional groups were tolerated. The practical applications of this reaction were further demonstrated by enlarged gram-scale and various derivations for complex heterocycles. Primary mechanistic studies suggested the involvement of cobalt-hydride mediated hydrogen atom transfer (HAT) process.

引用

页码：3372 / 3377

页数：6

共 50 条

[21] A Dual Cobalt and Photoredox Catalysis for Hydrohalogenation of Alkenes
Shibutani, Shotaro
Nagao, Kazunori
Ohmiya, Hirohisa
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (07) : 4375 - 4379
[22] Rh(iii)-Catalyzed and synergistic dual directing group-enabled redox-neutral [3+3] annulation of N-phenoxyacetamides with α-allenols
Chen, Fangyuan
Tang, Junyuan
Wei, Yinhui
Tian, Jingyuan
Gao, Hui
Yi, Wei
Zhou, Zhi
CHEMICAL COMMUNICATIONS, 2021, 57 (73) : 9284 - 9287
[23] Annulation of Benzamides with Arynes Using Palladium with Photoredox Dual Catalysis
Zhao, Jie
Li, Hongji
Li, Pinhua
Wang, Lei
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (14): : 9007 - 9016
[24] Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling
Nawrat, Christopher C.
Jamison, Christopher R.
Slutskyy, Yuriy
MacMillan, David W. C.
Overman, Larry E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (35) : 11270 - 11273
[25] Redox-Neutral Manganese(I)-Catalyzed C-H Activation: Traceless Directing Group Enabled Regioselective Annulation
Lu, Qingquan
Gressies, Steffen
Cembellin, Sara
Klauck, Felix J. R.
Daniliuc, Constantin G.
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) : 12778 - 12782
[26] Mild, Redox-Neutral Alkylation of !mines Enabled by an Organic Photocatalyst
Patel, Niki R.
Kelly, Christopher B.
Siegenfeld, Allison P.
Molander, Gary A.
ACS CATALYSIS, 2017, 7 (03): : 1766 - 1770
[27] Photocatalytic redox-neutral iqsoquinuclidine fragmentations enabled by visible light
Tucker, Joseph W.
Beatty, Joel W.
Stephenson, Corey R. J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[28] Photoredox/Cobalt Dual Catalysis Enabled Regiospecific Synthesis of Distally Unsaturated Ketones with Hydrogen Evolution
Wang, Xiaochuang
Li, Yi
Wu, Xuesong
ACS CATALYSIS, 2022, 12 (06) : 3710 - 3718
[29] Radical Decarboxylative Functionalizations Enabled by Dual Photoredox Catalysis
Huang, Hanchu
Jia, Kunfang
Chen, Yiyun
ACS CATALYSIS, 2016, 6 (08): : 4983 - 4988
[30] Redox-Neutral Rhodium(III)-Catalyzed Annulation of Arylhydrazines with Sulfoxonium Ylides To Synthesize 2-Arylindoles
Lv, Ningning
Chen, Zhengkai
Liu, Zhanxiang
Zhang, Yuhong
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13013 - 13021

← 1 2 3 4 5 →