Construction of a-Halogenated Boronic Esters via Visible Light-Induced C-H Bromination

被引：10

作者：

Gao, Feng-Chen ^{[1
]}

Li, Ming ^{[1
]}

Gu, Heng-Yu ^{[1
]}

Chen, Xin-Yi ^{[1
]}

Xu, Shuang ^{[1
]}

Wei, Yi ^{[1
]}

Hong, Kai ^{[1
,2
]}

机构：

[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

[2] East China Normal Univ, Shanghai Frontiers Sci Ctr Mol Intelligent Synth, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 19期

关键词：

CATALYZED BORYLATION; ASYMMETRIC-SYNTHESIS; HYDROGENATION; HOMOLOGATION; HALIDES; ACIDS; MECHANISM; SECONDARY; ADDITIONS; ACCESS;

D O I：

10.1021/acs.joc.3c01915

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

a-Halogenated boronic esters are versatile building blocks that can be diversified into a wide variety of polyfunctionalized molecules. However, their synthetic potential has been hampered by limited preparation methods. Herein, we report a visible light-induced C-H bromination reaction of readily available benzyl boronic esters. This method features high yields, mild conditions, simple operation, and good functional group tolerance. The analogous chlorides and iodides can be accessed via Finkelstein reaction. Synthesis of halogenated geminal diborons has also been demonstrated.

引用

页码：14246 / 14254

页数：9

共 50 条

[21] Site-Selective Aliphatic C-H Bromination Using N-Bromoamides and Visible Light
Schmidt, Valerie A.
Quinn, Ryan K.
Brusoe, Andrew T.
Alexanian, Erik J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) : 14389 - 14392
[22] Visible-Light- Induced Direct a C-H Functionalization of Alcohols
Zanda, Matteo
Niu, Linbin
Liu, Jiamei
Wang, Shengchun
Liang, Xing-An
Lei, Aiwen
SYNLETT, 2019, 30 (11) : A99 - A101
[23] Visible-light-induced halogenation of aliphatic C-H bonds
Tu, Haiyong
Zhu, Shengqing
Qing, Feng-Ling
Chu, Lingling
TETRAHEDRON LETTERS, 2018, 59 (03) : 173 - 179
[24] Visible-Light-Induced C-H Silylation of Azauracils with Hydrosilanes
Yu, Yongqi
You, Mengdan
Yu, Jiajia
Kong, Weiguang
Zhang, Chunyan
Bai, Jinjin
Li, Wenguang
Li, Ting
ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (01)
[25] Visible Light Induced Rhodium(I)-Catalyzed C-H Borylation
Thongpaen, Jompol
Manguin, Romane
Dorcet, Vincent
Vives, Thomas
Duhayon, Carine
Mauduit, Marc
Basle, Olivier
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (43) : 15244 - 15248
[26] Visible-light-induced photocatalytic difluoroacetylation of imidazopyridines via direct and regioselective C-H functionalization
Yin, Guojie
Zhu, Mei
Fu, Weijun
JOURNAL OF FLUORINE CHEMISTRY, 2017, 199 : 14 - 19
[27] Visible light-induced mono-bromination of arenes with BrCCl3
Fan, Jiali
Wei, Qiancheng
Zhu, Ershu
Gao, Jing
Cheng, Xiamin
Lu, Yongna
Loh, Teck-Peng
CHEMICAL COMMUNICATIONS, 2021, 57 (48) : 5977 - 5980
[28] Visible-Light-Induced Regioselective Dicarbonylation of Indolizines with Oxoaldehydes via Direct C-H Functionalization
Teng, Lili
Liu, Xiang
Guo, Pengfeng
Yu, Yue
Cao, Hua
ORGANIC LETTERS, 2020, 22 (10) : 3841 - 3845
[29] Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)2-H Coupling
Liang, Zhipeng
Wu, Ya-Nan
Wang, Yang
MOLECULES, 2022, 27 (17):
[30] Visible Light Induced C-H/N-H and C-X Bonds Reactions
Ahmad, Muhammad Siddique
Lin, Po-Han
Zhang, Qing
Zeng, Bing
Wang, Qifeng
Meguellati, Kamel
REACTIONS, 2023, 4 (01): : 189 - 230

← 1 2 3 4 5 →