Access to stereodefined (Z)-allylsilanes and (Z)-allylic alcohols via cobalt-catalyzed regioselective hydrosilylation of allenes.

Abstract:

:Hydrosilylation of allenes is the addition of a hydrogen atom and a silyl group to a carbon-carbon double bond of an allene molecule and represents a straightforward and atom-economical approach to prepare synthetically versatile allylsilanes and vinylsilanes. However, this reaction generally produces six possible isomeric organosilanes, and the biggest challenge in developing this reaction is to control both regioselectivity and stereoselectivity. The majorities of the developed allene hydrosilylation reactions show high selectivity towards the production of vinylsilanes or branched allylsilanes. By employing a cobalt catalyst generated from readily available and bench-stable cobalt precursor and phosphine-based ligands, here we show that this reaction proceeds under mild conditions in a regioselective and stereoselective manner, and affords synthetically challenging, but valuable linear cis-allylsilanes with excellent stereoselectivity (generally cis to trans ratios: >98:2). This cobalt-catalyzed (Z)-selective allene hydrosilylation provides a general approach to access molecules containing stereodefined (Z)-alkene units.

journal_name

Nat Commun

journal_title

Nature communications

authors

Wang C,Teo WJ,Ge S

doi

10.1038/s41467-017-02382-7

subject

Has Abstract

pub_date

2017-12-22 00:00:00

pages

2258

issue

1

issn

2041-1723

pii

10.1038/s41467-017-02382-7

journal_volume

8

pub_type

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