A Highly Efficient Pd(PPh3)4-Catalyzed Suzuki Cross-Coupling Method for the Preparation of 2-Nitrobiphenyls from 1-Chloro-2-nitrobenzenes and Phenylboronic Acids

被引：17
|
作者：
Elumalai, Vijayaragavan [1 ]
Sandtorv, Alexander H. [1 ]
Bjorsvik, Hans-Rene [1 ]
机构：
[1] Univ Bergen, Dept Chem, Allegaten 41, N-5007 Bergen, Norway
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 07期
关键词：
Synthetic methods; Homogeneous catalysis; Cross-coupling; Palladium; Multivariate regression analysis; TRANSITION-METAL-COMPLEXES; ARYL CHLORIDES; C-N; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; CARBAZOMYCIN-G; UNACTIVATED ARENES; MIYAURA REACTION; ACTIVE CATALYST; BOND FORMATION;
D O I：
10.1002/ejoc.201501487
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method for Suzuki cross-coupling of highly substituted and congested 1-chloro-2-nitrobenzene with phenylboronic acid was developed, investigated, and optimized. The reaction conditions comprises a mixture of MeOH and water (4:1) as the reaction medium, readily available and cheap Pd(PPh3)(4) as catalyst, sodium carbonate as base, and microwave heating, which affords a fast reaction rate with good outcomes. The procedure was proven to have high functional group tolerance with phenylboronic acid and for 1-chloro-2-nitrobenzene and thus is a general method for the synthesis of 2-nitrobiphenyl. The target scaffold, 2-nitrobiphenyls, was produced in excellent yields with excellent selectivities in all cases.
引用
收藏
页码：1344 / 1354
页数：11
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