86595-27-9Relevant articles and documents
PROCESS FOR SYNTHESIS OF DIALKOXYORGANOBORANES
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Page/Page column 9, (2008/06/13)
The invention relates to a process for the synthesis of dialkoxyorganoboranes, in particular to a process for the synthesis of dialkoxyorganoboranes by an ester exchange reaction. Moreover, the invention relates to a process for the synthesis of organo-oxazaborolidine catalysts (organo-CBS) and of trialkylboroxins. Furthermore, the invention relates to methods of using dialkoxyorganoboranes for the preparation of organo-CBS catalysts and in Suzuki-type coupling reactions.
Organoboranes. 31. A simple preparation of boronic esters from organolithium reagents and selected trialkoxyboranes
Brown, Herbert C.,Cole, Thomas E.
, p. 1316 - 1319 (2008/10/08)
The reaction of methyllithium with trimethoxyborane at -78°C in ethyl ether yields a mixture of methylated boranes and their corresponding ate complexes. We have found that under the same conditions triisopropoxyborane reacts cleanly with methyllithium to form the lithium methyltriisopropoxyborate complex. Protonation of this complex with anhydrous hydrogen chloride quantitatively yields methyl diisopropoxyborane. This reaction of organolithium reagent with triisopropoxyborane appears to provide a general, valuable route to boronic esters. Other alkoxyboranes were examined for their selectivity for monomethylation by methyllithium. In addition to triisopropoxyborane, triisobutoxyborane and tri-sec-butoxyborane also give the methylboronic esters quantitatively. This development provides the first general preparation of boronic esters from organolithium reagents.