Palladium-Catalyzed Cross-Coupling of Arylboronic Acid and Benzonitriles Using DMSO as the Methylene Source

被引：18

作者：

Ai, Han-Jun ^{[1
]}

Qi, Xinxin ^{[1
]}

Peng, Jin-Bao ^{[1
]}

Ying, Jun ^{[1
]}

Wu, Xiao-Feng ^{[1
,2
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Peoples R China

[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 10期

关键词：

palladium; amides; DMSO; cross-coupling; methylene sources; METAL-FREE CONDITIONS; DIMETHYL-SULFOXIDE; CONVENIENT ACCESS; METHYLATION; IMIDAZOHETEROCYCLES; FORMYLATION; REAGENT; KETONES;

D O I：

10.1002/ajoc.201800502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An interesting strategy on palladium-catalyzed cross-coupling of arylboronic acids and benzonitriles has been developed. In this approach, DMSO was utilized as the methylene source and reacted with benzamides (generated insitu from benzonitriles) to form an N-acyliminium cation, followed by palladium-catalyzed cross-coupling with phenylboronic acids to afford the final products. A variety of the desired products were obtained in moderate to excellent yield.

引用

页码：2045 / 2048

页数：4

共 50 条

[41] Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides
Blessley, George
Holden, Patrick
Walker, Matthew
Brown, John M.
Gouverneur, Veronique
ORGANIC LETTERS, 2012, 14 (11) : 2754 - 2757
[42] Palladium-Catalyzed Multialkynyl Cross-Coupling Reactions with Tetraalkynylindates
Kang, Dongjin
Eom, Dahan
Kim, Hyunseok
Lee, Phil Ho
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (12) : 2330 - 2336
[43] Palladium-catalyzed cross-coupling of organolead compounds with organostannanes
Kang, SK
Ryu, HC
Choi, SC
CHEMICAL COMMUNICATIONS, 1998, (12) : 1317 - 1318
[44] Palladium-catalyzed cross-coupling reactions in total synthesis
Nicolaou, KC
Bulger, PG
Sarlah, D
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) : 4442 - 4489
[45] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
Schmink, Jason R.
Krska, Shane W.
Tudge, Matthew T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[46] Palladium-catalyzed cross-coupling reaction of azides with isocyanides
Zhang, Zhen
Li, Zongyang
Fu, Bin
Zhang, Zhenhua
CHEMICAL COMMUNICATIONS, 2015, 51 (91) : 16312 - 16315
[47] Ionic Liquids in Palladium-Catalyzed Cross-Coupling Reactions
Mastrorilli, Piero
Monopoli, Antonio
Dell'Anna, Maria Michela
Latronico, Mario
Cotugno, Pietro
Nacci, Angelo
IONIC LIQUIDS (ILS) IN ORGANOMETALLIC CATALYSIS, 2015, 51 : 237 - 285
[48] Sesquiterpene metylenelactones in a palladium-catalyzed cross-coupling reaction
Belovodskii, A. V.
Shul'ts, E. E.
Shakirov, M. M.
Tolstikov, G. A.
DOKLADY CHEMISTRY, 2009, 426 : 138 - 142
[49] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
ALHASSAN, MI
SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
[50] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL CHLORIDES WITH ARYLSILATRANES
Yamamoto, Yutaro
Baralle, Alexandre
Godefroy, Anais
Murakami, Kei
Yorimitsu, Hideki
Osuka, Atsuhiro
HETEROCYCLES, 2017, 95 (01) : 568 - 574

← 1 2 3 4 5 →