FUNCTIONALIZED PRIMARY ALKYLTRIFLUOROBORATE SALTS AND METHOD FOR MAKING THE SAME

摘要

The invention provides methods for preparing boronic acids, for example, primary alkyl or alkenyl boronic acids, and alkali metal alkyl trifluoro borate salts, as described herein, wherein the primary alkyl boronic acids and the potassium alkyl trifluoroborate salts can contain one or more unprotected functional groups.

主权项

1. A method for synthesizing an substituted or unsubstituted alkylboronic acid or substituted or unsubstituted alkenyl boronic acid, comprising:
a) contacting a dialkylborane with a compound comprising a compound selected from the group consisting of an substituted or unsubstituted terminal alkene, and an substituted or unsubstituted alkyne to provide a mixed substituted or unsubstituted trialkylborane or an (substituted or unsubstituted alkenyl)dialkylborane; b) contacting the mixed substituted or unsubstituted trialkylborane or the (substituted or unsubstituted alkenyl)dialkylborane of step a) with at least two equivalents of an α,β-unsaturated carbonyl compound to provide an substituted or unsubstituted alkyl boronate diester or an substituted or unsubstituted alkenyl boronate diester; and c) contacting either water or an alcohol with the boronate diester to quench the reaction and to yield a corresponding boronic acid compound product or a corresponding alkoxyboronate diester product.