Synthesis of Alkylarylcarbinols via the Reaction of Organoboranes with Arylmethyl Chlorides

Abstract

(α-Chloroaryl)methyl anions, generated in situ by the deprotonation of arylmethyl chlorides with dicyclohexylamide, readily react with either trialkylboranes or alkylboronic esters to produce alkylarylcarbinols in good yields after oxidation. This reaction provides a very facile procedure for the synthesis of alkylarylcarbinols.

Sodium perborate and sodium percarbonate: further applications in organic synthesis

“…53 A route to alkylarylcarbinols from α,α-dichlorotoluenes and trialkylboranes also uses SPB in the work-up for oxidative cleavage of the organoborane. [54][55][56] The same overall transformation can be effected using the corresponding benzaldehyde trisyl-57 or tosylhydrazone 58 as the source of the aryl moiety, with yields generally being superior with the trisyl series. (Scheme 15).…”