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
收藏
页码：2045 / 2048
页数：4
相关论文
共 50 条
  • [21] Palladium-catalyzed cross-coupling reactions of arylboronic acids and 2-I-p-carborane
    Eriksson, L
    Beletskaya, IP
    Bregadze, VI
    Sivaev, IB
    Sjöberg, S
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 657 (1-2) : 267 - 272
  • [22] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES
    ALI, NM
    MCKILLOP, A
    MITCHELL, MB
    REBELO, RA
    WALLBANK, PJ
    TETRAHEDRON, 1992, 48 (37) : 8117 - 8126
  • [23] Palladium-Catalyzed Cross-Coupling of 2-Chloroquinoxaline N-Oxides with Arylboronic Acids
    Maichrowski, Jan
    Huebner, Eike G.
    Kaufmann, Dieter E.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (36) : 8185 - 8196
  • [24] Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source
    Lyu, Xue
    Sun, Guanglong
    Zhou, Yang
    Wang, Yingying
    Lei, Min
    Wu, Wanying
    Guo, Dean
    MONATSHEFTE FUR CHEMIE, 2019, 150 (02): : 309 - 315
  • [25] Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source
    Xue Lyu
    Guanglong Sun
    Yang Zhou
    Yingying Wang
    Min Lei
    Wanying Wu
    Dean Guo
    Monatshefte für Chemie - Chemical Monthly, 2019, 150 : 309 - 315
  • [26] PALLADIUM-CATALYZED CROSS-COUPLING OF PHENYLBORONIC ACID WITH HETEROCYCLIC AROMATIC HALIDES
    STAVENUITER, J
    HAMZINK, M
    VANDERHULST, R
    ZOMER, G
    WESTRA, G
    KRIEK, E
    HETEROCYCLES, 1987, 26 (10) : 2711 - 2716
  • [27] Palladium-Catalyzed Carboauration of Alkynes and Palladium/Gold Cross-Coupling
    Shi, Yili
    Ramgren, Stephen D.
    Blum, Suzanne A.
    ORGANOMETALLICS, 2009, 28 (05) : 1275 - 1277
  • [28] Palladium-Catalyzed Oxidative Cross-Coupling Reaction of Arylboronic Acids with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates
    Tsoi, Yuk-Tai
    Zhou, Zhongyuan
    Chan, Albert S. C.
    Yu, Wing-Yiu
    ORGANIC LETTERS, 2010, 12 (20) : 4506 - 4509
  • [29] STOICHIOMETRIC SYNTHESIS OF UNSYMMETRICAL MONONITROBIPHENYLS VIA THE PALLADIUM-CATALYZED CROSS-COUPLING OF ARYLBORONIC ACIDS WITH ARYL BROMIDES
    MILLER, RB
    DUGAR, S
    ORGANOMETALLICS, 1984, 3 (08) : 1261 - 1263
  • [30] Palladium-Catalyzed Cross-Coupling of Aryl Halides Using Organotitanium Nucleophiles
    Lee, Hang Wai
    Lam, Fuk Loi
    So, Chau Ming
    Lau, Chak Po
    Chan, Albert S. C.
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) : 7436 - 7439
12345