Palladium-catalyzed borylation of aryl (pseudo)halides and its applications in biaryl synthesis

Hong Ji,Jianghong Cai,Nana Gan,Liyang Wu,Zhaohua Wang,Tao Yi,Guorong Li

doi:10.1186/s13065-018-0510-6

Hong Ji, Jianghong Cai + Show 5 more

Open Access

https://doi.org/10.1186/s13065-018-0510-6

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Abstract

A facile and efficient palladium-catalyzed borylation of aryl (pseudo)halides at room temperature has been developed. Arylboronic esters were expeditiously assembled in good yields and with a broad substrate scope and good functional group compatibility. This approach has been successfully applied to the one-pot two-step borylation/Suzuki–Miyaura cross-coupling reaction, providing a concise access to biaryl compounds from readily available aryl halides. Furthermore, a parallel synthesis of biaryl analogs is accomplished at room temperature using the strategy, which enhances the practical usefulness of this method.

Highlights

Arylboronic acids and esters are versatile reagents in organic synthesis
Palladium-catalyzed synthesis of arylboronic esters from aryl halides or pseudo-halides has opened the door for the development of efficient
A facile single pot synthesis of biaryl and biheteroaryl compounds via sequential borylation and Suzuki–Miyaura cross coupling reaction was presented

Summary

Introduction

Arylboronic acids and esters are versatile reagents in organic synthesis. They were widely used in C–C, C–O, C–N and C–S bond forming reactions [1, 2], which are essential for the construction of bioactive molecules and organic building blocks. Palladium-catalyzed synthesis of arylboronic esters from aryl halides or pseudo-halides has opened the door for the development of efficient. The palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of arylboronic acids or esters with aryl halides has become the most common and powerful method to build such structures [28, 32,33,34]. Since one-pot twostep protocol combining borylation and Suzuki–Miyaura cross coupling steps was reported in 2004 [35], the need to prepare or purchase a boronic acid or ester could be eliminated. We reported a highly practical and efficient method for palladium-catalyzed borylation of aryl halides or pseudo-halides at room temperature. A facile single pot synthesis of biaryl and biheteroaryl compounds via sequential borylation and Suzuki–Miyaura cross coupling reaction was presented. The approach has been successfully applied in formats amenable to parallel synthesis of biaryls

Results and discussion

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Conclusion