62930-28-3Relevant academic research and scientific papers
Organoboranes. 44. A more convenient, practical route to achieve the homologation of boronic esters
Brown, Herbert C.,Singh, Shankar M.
, p. 994 - 997 (2008/10/08)
A more practical procedure has been developed for the homologation of boronic esters, utilizing the in situ formation of (dichloromethyl)lithium at -78°C from dichloromethane and one of the bases, lithium diisopropylamide (LDA) or lithium 2,2′,6,6′-tetramethylpiperidide (LTMP), followed by in situ reduction of the α-chloroboronic ester intermediates with potassium triisopropoxyborohydride (KIPBH). This procedure is relatively more practical for large-scale applications and avoids both the low temperature (-100°C) and the use of an equivalent of alkyllithium required by the earlier procedure. The reaction is broadly applicable to many of the boronic esters tested with the earlier procedure.
