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Pure Appl. Chem., 2003, Vol. 75, No. 9, pp. 1231-1237

http://dx.doi.org/10.1351/pac200375091231

Use of organoboron halides in organic synthesis

G. W. Kabalka, Z. Wu and Y. Ju

Departments of Chemistry and Radiology, University of Tennessee, Knoxville, TN 37996-1600, USA

Abstract: Several new organic transformations have been achieved utilizing boron halide reagents. Aryl aldehydes are conveniently converted to gem-dichloromethylbenzenes using boron trichloride. Aryl aldehydes are alkylated by alkylboron chlorides in a Grignard-like fashion to generate the corresponding arylalkanols or alkylboron chlorides. Aryl aldehydes react with divinylboron halides (generated via the haloboration of alkynes) to produce 1,5-di-halo-1,4-dienes in excellent yields.