Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles

被引：76

作者：

Vasilopoulos, Aristidis ^{[1
]}

Golden, Dung L. ^{[1
]}

Buss, Joshua A. ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

关键词：

BONDS; ACTIVATION; AMINATION; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.0c02238

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Site-selective transformation of benzylic C-H bonds into diverse functional groups is achieved via Cu-catalyzed C-H fluorination with N-fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C-O, C-N, and C-C coupling reactions.

引用

页码：5753 / 5757

页数：5

共 50 条

[31] Copper-Catalyzed Benzylic C-H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2-Arylbenzothiazoles
Yu, Wentao
Wu, Wanqing
Jiang, Huanfeng
CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (11) : 1158 - 1166
[32] Copper-Catalyzed Benzylic C-H Cross-Coupling Enabled by Redox Buffers: Expanding Synthetic Access to Three-Dimensional Chemical Space
Chen, Si-Jie
Krska, Shane W.
Stahl, Shannon S.
ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (24) : 3604 - 3615
[33] Electrochemical Benzylic C-H Functionalization with Isocyanides
Tang, Shanyu
Guillot, Regis
Grimaud, Laurence
Vitale, Maxime R.
Vincent, Guillaume
ORGANIC LETTERS, 2022, 24 (11) : 2125 - 2130
[34] Copper-catalyzed C-N coupling/C-H functionalization: A tandem approach to azole-fused quinazoline derivatives
Chen, Dingben
Huang, Ling
Yang, Jianguo
Ma, Junna
Zheng, Yingying
Luo, Yi
Shen, Yang
Wu, Jiashou
Feng, Chao
Lv, Xin
TETRAHEDRON LETTERS, 2018, 59 (21) : 2005 - 2009
[35] Enantioselective Copper-Catalyzed Alkynylation of Benzylic C-H Bonds via Radical Relay
Fu, Liang
Zhang, Zhihan
Chen, Pinhong
Lin, Zhenyang
Liu, Guosheng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (28) : 12493 - 12500
[36] Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes
Mitsuda, Shinobu
Fujiwara, Taiki
Kimigafukuro, Katsuyoshi
Monguchi, Daiki
Mori, Atsunori
TETRAHEDRON, 2012, 68 (18) : 3585 - 3590
[37] Enantioselective Cyanation of Benzylic C-H Bonds via Copper-Catalyzed Radical Delay
Ding, Kuiling
PROGRESS IN CHEMISTRY, 2017, 29 (01) : 13 - 14
[38] Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay
Zhang, Wen
Wang, Fei
McCann, Scott D.
Wang, Dinghai
Chen, Pinhong
Stahl, Shannon S.
Liu, Guosheng
SCIENCE, 2016, 353 (6303) : 1014 - 1018
[39] Copper-Catalyzed C7-Selective C-H/N-H Cross-Dehydrogenative Coupling of Indolines with Sulfoximines
Banerjee, Sonbidya
Mishra, Manmath
Punniyamurthy, Tharmalingam
ORGANIC LETTERS, 2022, : 7997 - 8001
[40] Copper-Catalyzed Amination of Primary Benzylic C-H Bonds with Primary and Secondary Sulfonamides
Powell, David A.
Fan, Hope
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) : 2726 - 2729

← 1 2 3 4 5 →