Abstract
Recent years have witnessed the growing interest in the remote functionalization of alkenes for it offers a strategy to activate the challenging C–H bonds distant from the initiation point via alkene isomerization/functionalization. However, the catalytic enantioselective isomerization/functionalization with one single transition metal catalyst remains rare. Here we report a highly regio- and enantioselective cobalt-catalyzed remote C–H bond borylation of internal alkenes via sequential alkene isomerization/hydroboration. A chiral ligand featured twisted pincer, anionic, and non-rigid characters is designed and used for this transformation. This methodology, which is operationally simple using low catalyst loading without additional activator, shows excellent enantioselectivity and can be used to convert various internal alkenes with regio- and stereoisomers to valuable chiral secondary organoboronates with good functional group tolerance.
Highlights
Recent years have witnessed the growing interest in the remote functionalization of alkenes for it offers a strategy to activate the challenging C–H bonds distant from the initiation point via alkene isomerization/functionalization
Recent years have witnessed the important progress in the field of catalytic alkene isomerization/functionalization with various coupling reagents[5,16], such as ArX17–19, CO220,21, CO/H222, HBpin[23,24,25,26], R3SiH27–29, and so on[11,30,31], to afford the corresponding coupling products
The catalytic enantioselective isomerization/functionalization with one single transition metal catalyst is restricted to only few examples[5,16]
Summary
Recent years have witnessed the growing interest in the remote functionalization of alkenes for it offers a strategy to activate the challenging C–H bonds distant from the initiation point via alkene isomerization/functionalization. The development of asymmetric alkene isomerization/functionalization processes using single catalyst system is highly desirable. We have developed a cobalt-catalyzed asymmetric sequential hydroboration/hydrogenation of internal alkynes, affording a series of chiral secondary organoboronates[56].
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