Copper‐Catalyzed Cross‐Coupling of Benzylic Bromides with Arylboronic Acids: Synthesis of Diarylalkanes and Preliminary Antifungal Evaluation Against Magnaporthe Grisea. Issue 4 (20th February 2020)

• Record Type: Journal Article
• Authors: Zhu, Zhu; Liu, Jinggong; Dong, Shoucheng; Chen, Bolai; Wang, Zhenghui; Tang, Ri‐yuan; Li, Zhaodong
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 4(2020)
• Page Start: 631
• Page End: 636
• Publication Date: 2020-02-20
• Subjects: copper -- cross-coupling -- homogeneous catalysis -- radicals -- antibacterial evaluation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000007
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Reported herein is the practical synthesis of 1, 1‐diarylalkanes motifs via copper‐catalyzed cross‐coupling reaction of benzylic bromides with arylboronic acids under mild conditions. The protocols show broad scope and good functional group tolerance, and are also applicable to complex natural products. Mechanistic study indicates a radical mechanism. Moreover, preliminary antibacterial evaluation against Magnaporthe grisea is also described for the first time. Abstract : A copper‐catalyzed Suzuki‐Miyaura‐type cross‐coupling of benzyl bromides with arylboronic acids using bidentate nitrogen ligand is described herein. Numerous aryl boronic acids as well as more challenging secondary acyclic and cyclic benzyl bromides could be successfully converted into the corresponding 1, 1‐diarylalkanes motifs. The reaction has been successfully applied to the late stage functionalization of natural product derivatives, and mechanistic study indicates a radical mechanism. Moreover, preliminary antibacterial evaluation against Magnaporthe grisea shows an inhibitory rate of up to 46%.