Enantioselective Aerobic Oxidative C(sp3)-H Olefination of Amines via Cooperative Photoredox and Asymmetric Catalysis

被引：115

作者：

Wei, Guo ^{[1
]}

Zhang, Chenhao ^{[1
]}

Bures, Filip ^{[2
]}

Ye, Xinyi ^{[3
]}

Tan, Choon-Hong ^{[3
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Univ Pardubice, Fac Chem Technol, Inst Organ Chem & Technol, Studentska 573, Pardubice 53210, Czech Republic

[3] Nanyang Technol Univ, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

来源：

ACS CATALYSIS | 2016年 / 6卷 / 06期

关键词：

asymmetric cooperative catalysis; photoredox catalysis; organocatalysis; aerobic oxidative olefination; beta-carbolines; C-H BONDS; DUAL-CATALYSIS; CYCLIC IMINES; FUNCTIONALIZATION; ORGANOCATALYSIS; ACID; PHOTOCATALYSIS; HYDROGENATION; ALKYLATION; ACTIVATION;

D O I：

10.1021/acscatal.6b00846

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：

A cooperative photoredox and asymmetric catalysis for the enantioselective aerobic oxidative C(sp(3))-H olefination of tetrahydro-beta-carbolines (THCs) is reported. This method, which is also effective for tetrahydroisoquinolines (THIQs), features a triple-catalyst strategy, involving a dicyanopyrazine-derived chromophore (DPZ) as the metal-free photoredox catalyst, a chiral Lewis base catalyst, and an inorganic salt cocatalyst. The current protocol provides straightforward access to a series of valuable a-substituted THCs and THIQs in high yields with excellent regio- and enantioselectivities (up to 95% ee).

引用

页码：3708 / 3712

页数：5

共 50 条

[31] Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
Yufan Liang
Xiaheng Zhang
David W. C. MacMillan
Nature, 2018, 559 : 83 - 88
[32] Site-selective remote C(sp3)–H heteroarylation of amides via organic photoredox catalysis
Hui Chen
Wenjing Fan
Xiang-Ai Yuan
Shouyun Yu
Nature Communications, 10
[33] Amidyl Radical Directed γ-C(sp3)-H Functionalization with Silyl Enol Ethers via Photoredox Catalysis
Xu, Kedong
Yang, Jiawen
Qin, Haitao
Liu, Feng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (31)
[34] Direct Acylation of C(sp3)-H Bonds Enabled by Nickel and Photoredox Catalysis
Joe, Candice L.
Doyle, Abigail G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (12) : 4040 - 4043
[35] Site-selective remote C(sp3)-H heteroarylation of amides via organic photoredox catalysis
Chen, Hui
Fan, Wenjing
Yuan, Xiang-Ai
Yu, Shouyun
NATURE COMMUNICATIONS, 2019, 10 (1)
[36] Functionalization of Unactivated C(sp3)-H Bond via Paired Oxidative and Reductive Catalysis
Chang Rui
Ye Juntao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (07) : 2586 - 2588
[37] Aerobic Oxidation of Benzylic sp3 C-H Bonds through Cooperative Visible-Light Photoredox Catalysis of N-Hydroxyimide and Dicyanopyrazine
Liu, Xinfei
Lin, Lu
Ye, Xinyi
Tan, Choon-Hong
Jiang, Zhiyong
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) : 422 - 425
[38] Mechanistic Insights into Enantioselective C(sp3)-H Acylation to Construct α-Amino Ketones via Photoredox and Ni(II) Dual Catalysis: A DFT Study
Liu, Ran
Lv, Kang
Bao, Xiaoguang
CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (08)
[39] C(sp3)-H versus C(sp3)-C(sp) in Activation of Propargylic Amines under Transition-Metal Catalysis
Nakamura, Hiroyuki
SYNLETT, 2015, 26 (12) : 1649 - 1664
[40] Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines
Jiang, Heng
He, Jian
Liu, Tao
Yu, Jin-Quan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) : 2055 - 2059

← 1 2 3 4 5 →