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. Issue 7 (8th February 2016)

• Record Type: Journal Article
• Authors: Elumalai, Vijayaragavan; Sandtorv, Alexander H.; Bjørsvik, Hans‐René
• Is Part Of: European journal of organic chemistry. Issue 7(2016)
• Page Start: 1344
• Page End: 1354
• Publication Date: 2016-02-08
• Subjects: Synthetic methods -- Homogeneous catalysis -- Cross‐coupling -- Palladium -- Multivariate regression analysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501487
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : An efficient microwave‐assisted and Pd(PPh3 )4 ‐catalyzed Suzuki cross‐coupling method for the synthesis of 2‐nitrobiphenyls from 1‐chloro‐2‐nitrobenzenes and phenylboronic acids is disclosed. The method exhibits excellent selectivity and fast reaction rates, provides high to excellent yields, and tolerates both electron‐withdrawing and ‐donating groups.