N-heterocyclic carbene palladium(II)-catalyzed Suzuki-Miyaura cross coupling of N-acylsuccinimides by C-N cleavage

被引：16

作者：

Wang, Tao ^{[1
,2
]}

Guo, Jiarui ^{[1
,2
]}

Wang, Hengjin ^{[1
,2
]}

Guo, Han ^{[1
,2
]}

Jia, Dingli ^{[1
,2
]}

Zhang, Wen ^{[1
,2
]}

Liu, Lantao ^{[1
,2
]}

机构：

[1] Shangqiu Normal Univ, Sch Chem & Chem Engn, Henan Engn Lab Green Synth Pharmaceut, Shangqiu 476000, Henan, Peoples R China

[2] Shangqiu Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Biomol Recognit & Sensing, Shangqiu 476000, Henan, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2018年 / 877卷

基金：

中国国家自然科学基金;

关键词：

ACYL-TRANSFER REAGENTS; CARBOXYLIC ANHYDRIDES; ORGANOBORON COMPOUNDS; ARYLBORONIC ACIDS; CARBENE-PALLADIUM(II) COMPLEXES; KETONE SYNTHESIS; BOND ACTIVATION; O BONDS; ESTERS; AMIDES;

D O I：

10.1016/j.jorganchem.2018.09.026

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An easily prepared, well-defined N-heterocyclic carbene-palladium(II) complex was found to be an efficient catalyst for the Suzuki-Miyaura cross-coupling of N-acylsuccinimides with arylboronic acids via C-N bond activation. Under the optimal conditions, all reactions proceeded smoothly generating broad array of diaryl ketones in good to high yields (81->99%) within hours. (c) 2018 Elsevier B.V. All rights reserved.

引用

页码：80 / 84

页数：5

共 38 条

[1] A Cross-Coupling Approach to Amide Bond Formation from Esters
Ben Halima, Taoufik
Vandavasi, Jaya Kishore
Shkoor, Mohanad
Newman, Stephen G.
[J]. ACS CATALYSIS, 2017, 7 (03): : 2176 - 2180
[2] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
Ben Halima, Taoufik
Zhang, Wanying
Yalaoui, Imane
Hong, Xin
Yang, Yun-Fang
Houk, Kendall N.
Newman, Stephen G.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1311 - 1318
[3] Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
Blangetti, Marco
Rosso, Helena
Prandi, Cristina
Deagostino, Annamaria
Venturello, Paolo
[J]. MOLECULES, 2013, 18 (01) : 1188 - 1213
[4] Palladium-catalyzed reactions of organoboron compounds with acyl chlorides
Bykov, VV
Korolev, DN
Bumagin, NA
[J]. RUSSIAN CHEMICAL BULLETIN, 1997, 46 (09) : 1631 - 1632
[5] Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids
Chen, Qiang
Fan, Xin-Heng
Zhang, Li-Peng
Yang, Lian-Ming
[J]. RSC ADVANCES, 2014, 4 (96) : 53885 - 53890
[6] Malabaricone C from Myristica cinnamomea Exhibits Anti-Quorum Sensing Activity
Chong, Yee Meng
Yin, Wai Fong
Ho, Chia Yong
Mustafa, Mohamad Rais
Hadi, A. Hamid A.
Awang, Khalijah
Narrima, Putri
Koh, Chong-Lek
Appleton, David R.
Chan, Kok-Gan
[J]. JOURNAL OF NATURAL PRODUCTS, 2011, 74 (10): : 2261 - 2264
[7] N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C-N cleavage
Cui, Ming
Chen, Zeyu
Liu, Tingting
Wang, Hui
Zeng, Zhuo
[J]. TETRAHEDRON LETTERS, 2017, 58 (40) : 3819 - 3822
[8] Breaking Amides using Nickel Catalysis
Dander, Jacob E.
Garg, Neil K.
[J]. ACS CATALYSIS, 2017, 7 (02): : 1413 - 1423
[9] Conjugates of 2,4-Dihydroxybenzoate and Salicylhydroxamate and Lipocations Display Potent Antiparasite Effects by Efficiently Targeting the Trypanosoma brucei and Trypanosoma congolense Mitochondrion
Fueyo Gonzalez, Francisco Jose
Ebiloma, Godwin U.
Izquierdo Garcia, Carolina
Bruggeman, Victor
Sanchez Villamanan, Jose Maria
Donachie, Anne
Balogun, Emmanuel Oluwadare
Inaoka, Daniel Ken
Shiba, Tomoo
Harada, Shigeharu
Kita, Kiyoshi
de Koning, Harry P.
Dardonville, Christophe
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (04) : 1509 - 1522
[10] Decarbonylative Silylation of Esters by Combined Nickel and Copper Catalysis for the Synthesis of Arylsilanes and Heteroarylsilanes
Guo, Lin
Chatupheeraphat, Adisak
Rueping, Magnus
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 11810 - 11813

← 1 2 3 4 →