ARTICLE
Access to stereodefined (Z)-allylsilanes and (Z)-
allylic alcohols via cobalt-catalyzed regioselective
hydrosilylation of allenes
Chao Wang
1
, Wei Jie Teo
1
& Shaozhong Ge
1
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 big-
gest challenge in developing this reaction is to control both regioselectivity and stereo-
selectivity. 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.
DOI: 10.1038/s41467-017-02382-7
OPEN
1
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore. Correspondence and requests for materials
should be addressed to S.G. (email: chmgsh@nus.edu.sg)
NATURE COMMUNICATIONS
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8: 2258
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DOI: 10.1038/s41467-017-02382-7
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www.nature.com/naturecommunications
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