Application of arylboronic acid in organic synthesis.

Abstract

A review. The applications of arylboronic acid in biaryl synthesis, synthesis of diaryl ethers, synthesis of arom. amines and catalytic addn. reactions were summarized. Suzuki cross-coupling reaction is one of the most efficient methods for the construction of C(aryl)-C(aryl) bonds. In recent years, various efficient catalyst precursors have been developed that allow aryl iodides, bromides, and chlorides to be effectively coupled with aryl boronic acids. Moreover, Ni-based catalysts have also been successfully used for the Suzuki reaction of aryl chlorides. Coupling of phenols and arylboronic acids in presence of Cu(OAc)2 and NEt3 give diaryl ethers. The catalytic coupling of arylboronic acids and amines is an effective C-N coupling method. The 1,4-conjugate addn. of arylboronic acids to enones is widely used process for carbon-carbon bond formation giving β-substituted carbonyl compds. with high enantioselectivity. These reactions show good substrate generality while using relatively nontoxic, inexpensive reagents under mild conditions and provide the products in good yield. [on SciFinder(R)]