Solvent-switchable regioselective 1,2-or 1,6-addition of quinones with boronic acids

被引：2

作者：

Xia, Qi ^{[1
]}

Zhou, Yaxuan ^{[1
]}

Yang, Xiaoning ^{[1
]}

Zhang, Yanqiu ^{[1
]}

Wang, Jiayi ^{[1
]}

Song, Gonghua ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 54期

关键词：

C-H ARYLATION; BIOSYNTHESIS;

D O I：

10.1039/d3cc01968c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient copper-catalyzed solvent-switchable regioselective 1,2- or 1,6-addition of quinones with boronic acids has been developed. This novel catalytic protocol for the synthesis of various quinols and 4-phenoxyphenols was enabled by a simple solvent swap between H2O and MeOH. It features mild reaction conditions, simple and easy operation, broad substrate scope and excellent regioselectivity. The gram-scale reactions as well as the further transformations of both addition products were also successfully investigated.

引用

页码：8416 / 8419

页数：4

共 50 条

[31] 1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
Gao, Shang
Xu, Xiuyan
Yuan, Zhenbo
Zhou, Haipin
Yao, Hequan
Lin, Aijun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 3006 - 3012
[32] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
Chauhan, Pankaj
Kaya, Ugur
Enders, Dieter
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912
[33] DBU-catalyzed 1,6-addition of quinazolinones and quinolones to para quinone methides
Zhang, Zhiguang
Tan, Xiaoyu
Sui, Ao
Zhang, Bingzhu
Zhang, Yong
TETRAHEDRON LETTERS, 2022, 110
[34] Rhodium-catalyzed asymmetric 1,6-addition of aryl zinc reagents to dienones
Hayashi, T
Yamamoto, S
Tokunaga, N
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) : 4224 - 4227
[35] 1,6-ADDITION OF T-BUTYLMAGNESIUM CHLORIDE TO 9,10-PHENANTHRAQUINONE
CAMERON, DW
MINGIN, M
AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (04) : 859 - 863
[36] 1,4-ADDITION OF GRIGNARD-REAGENTS AND 1,6-ADDITION OF LITHIUM ORGANOCUPRATES TO N,N-DIETHYLSORBAMIDE
BARBOT, F
KADIBELBAN, A
MIGINIAC, P
TETRAHEDRON LETTERS, 1983, 24 (46) : 5089 - 5090
[37] 1,6-Addition of Tertiary Carbon Radicals Generated From Alcohols or Carboxylic Acids by Visible-Light Photoredox Catalysis
Abbas, Samir Y.
Zhao, Peng
Overman, Larry E.
ORGANIC LETTERS, 2018, 20 (03) : 868 - 871
[38] Photoredox deoxygenative allylation of carboxylic acids via selective 1,6-addition of acyl radicals to electron-deficient 1,3-dienes
Zhang, Lili
Li, Yuhang
Guo, Zhenyu
Li, Yantao
Li, Nian
Li, Weipeng
Zhu, Chengjian
Xie, Jin
CHINESE JOURNAL OF CATALYSIS, 2023, 50 : 215 - 221
[39] Regioselective 1,6-conjugate addition of organocuprate reagents to γ-alkylidenebutenolides
Vivien, Anthony
Bartoli, Alexandra
Parrain, Jean-Luc
Commeiras, Laurent
TETRAHEDRON LETTERS, 2020, 61 (06)
[40] ADDITION OF DIALKYLPHOSPHOROUS ACIDS TO 1,6-HEXAMETHYLENEDIISOCYANATE
KUZNETSOV, E
BAKHITOV, MI
ZHURNAL OBSHCHEI KHIMII, 1961, 31 (09): : 3015 - &

← 1 2 3 4 5 →