摘要：

Reactions of sodium tetraarylborates and arylboronic acids with acyl chlorides in the presence of palladium salts afford non-symmetrical ketones in high yields under mild conditions.Cross-coupling of organoboron compounds with organic electrophiles catalyzed by palladium and nickel complexes (the Suzuki reaction)is currently one of the most attractive methods for the formation of new carbon-carbon bonds,which is widely used in organic synthesis.1 In water or water-organic solvent mixtures,the Suzuki reaction is very effectively catalyzed by palladium salts PdX2 containing no phosphine ligands.2 "Ligand-free"palladium was successfully used as a catalyst for reactions of sterically hindered tris(l-naphthyl)borane with aryl halides and diaryliodonium salts.3 It was interesting to apply this approach to the synthesis of non-symmetrical ketones by reactions of organoboron compounds with acyl chlorides as electrophilic reagents.This approach has been employed4 for acyldeboration of sodium tetraphenylborate with various RCOCI in THF in the presence of Pd(PPh3)4 at 25 deg C.However,under these conditions,only one phenyl group of Ph4BNa is involved in the reaction.Later,it was shown that arylboronic acids5 and triorganoboranes6 can also be used in cross-coupling with acyl chlorides under similar conditions.Earlier,we found that in the presence of ligand-free palladium,sodium tetraarylborates and arylboronic acids react with acyl chlorides under very mild conditions to give non-symmetrical ketones in high yields.7 According to the published data,8 the Suzuki reaction catalyzed by phosphine complexes of palladium requires more drastic conditions and proceeds more slowly.In the present work,the synthetic aspects of this reaction and some of its specific features are described in detail.

展开