Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne

Yuuya Kawasaki; Youhei Ishikawa; Kazunobu Igawa; Katsuhiko Tomooka

doi:10.1021/ja209553f

Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne

Yuuya Kawasaki, Youhei Ishikawa, Kazunobu Igawa, Katsuhiko Tomooka

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

77 Citations (Scopus)

Abstract

Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

Original language	English
Pages (from-to)	20712-20715
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	51
DOIs	https://doi.org/10.1021/ja209553f
Publication status	Published - Dec 28 2011

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja209553f

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title = "Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne",

abstract = "Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.",

author = "Yuuya Kawasaki and Youhei Ishikawa and Kazunobu Igawa and Katsuhiko Tomooka",

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T1 - Directing group-controlled hydrosilylation

T2 - Regioselective functionalization of alkyne

AU - Kawasaki, Yuuya

AU - Ishikawa, Youhei

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

PY - 2011/12/28

Y1 - 2011/12/28

N2 - Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

AB - Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

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Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne

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