Organic compounds bearing both silyl and boryl groups
are important
building blocks in organic synthesis because of the adequate reactivity
of the silyl and boryl groups and high stereospecificity in their
derivatization reactions. The difference in reactivity between the
silyl and boryl groups enables stepwise derivatization of these groups
to afford complex molecules. Here, we report the copper(I)-catalyzed
silaboration of terminal allenes to produce multisubstituted allylic
boronates embedded with an alkenyl silane structure. The reaction
can proceed with a variety of allenes and silylboranes. Furthermore,
the silyl and boryl groups were successfully converted into other
functional groups, while retaining the stereochemistry of the alkene
moiety.
A copper(I)-catalyzed intermolecular alkylboration of terminal allenes using unactivated alkyl halides as the carbon electrophiles is reported. The regio- and stereochemistry of the product, (Z)-alkenyl boronate, could be constructed without...
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.