Vinylmetalloids. II. The high regioselectivity of dialkylboranes in the hydroboration of vinyltrimethylsilane

John A. Soderquist; Alfred Hassner

doi:10.1016/S0022-328X(00)84889-5

Vinylmetalloids. II. The high regioselectivity of dialkylboranes in the hydroboration of vinyltrimethylsilane

John A. Soderquist
, Alfred Hassner

Purdue University
State University of New York Binghamton University

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

30 Scopus citations

Abstract

Dialkylboranes such as disiamylborane, dicyclohexylborane and 9-borabicyclo[3.3.1]nonane add cleanly to vinyltrimethylsilane (I) with high regiospecificity (≥ 95%) to give the corresponding β-silylethylboranes, valuable intermediates in the synthesis of functionalized organosilanes. Oxidation of these adducts provides a convenient, high-yield route to 2-trimethylsilylethanol (IIβ). Reduction of acetyltrimethylsilane (IX) with borane-tetrahydrofuran provides a simple route to the isomeric 1-trimethylsilylethanol (IIα). These new developments illustrate the utility of borane reagents in the regiospecific syntheses of trimethylsilylethanols (II).

Original language	English
Pages (from-to)	C12-C16
Journal	Journal of Organometallic Chemistry
Volume	156
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(00)84889-5
State	Published - 15 Aug 1978
Externally published	Yes

Bibliographical note

Funding Information:
The stimulating conversations and helpful suggestions of Professor H.C. Brown, Dr. J.L. Hubbard, Dr. S. Krishnamurthy, Mr. J. Campbell, Mr. S.U. Kulkarni, Mr. K.L. Thompson and Mr. K.K. Wang regarding this work are gratefully acknowledged. Support for this work from NC1 Grant CA-19203 and NSF Grant CHE-76-20846 is appreciated.

Funding

The stimulating conversations and helpful suggestions of Professor H.C. Brown, Dr. J.L. Hubbard, Dr. S. Krishnamurthy, Mr. J. Campbell, Mr. S.U. Kulkarni, Mr. K.L. Thompson and Mr. K.K. Wang regarding this work are gratefully acknowledged. Support for this work from NC1 Grant CA-19203 and NSF Grant CHE-76-20846 is appreciated.

Funders	Funder number
NC1	CA-19203
National Science Foundation	CHE-76-20846

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10.1016/S0022-328X(00)84889-5

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title = "Vinylmetalloids. II. The high regioselectivity of dialkylboranes in the hydroboration of vinyltrimethylsilane",

abstract = "Dialkylboranes such as disiamylborane, dicyclohexylborane and 9-borabicyclo[3.3.1]nonane add cleanly to vinyltrimethylsilane (I) with high regiospecificity (≥ 95\%) to give the corresponding β-silylethylboranes, valuable intermediates in the synthesis of functionalized organosilanes. Oxidation of these adducts provides a convenient, high-yield route to 2-trimethylsilylethanol (IIβ). Reduction of acetyltrimethylsilane (IX) with borane-tetrahydrofuran provides a simple route to the isomeric 1-trimethylsilylethanol (IIα). These new developments illustrate the utility of borane reagents in the regiospecific syntheses of trimethylsilylethanols (II).",

author = "Soderquist, \{John A.\} and Alfred Hassner",

note = "Funding Information: The stimulating conversations and helpful suggestions of Professor H.C. Brown, Dr. J.L. Hubbard, Dr. S. Krishnamurthy, Mr. J. Campbell, Mr. S.U. Kulkarni, Mr. K.L. Thompson and Mr. K.K. Wang regarding this work are gratefully acknowledged. Support for this work from NC1 Grant CA-19203 and NSF Grant CHE-76-20846 is appreciated.",

year = "1978",

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doi = "10.1016/S0022-328X(00)84889-5",

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Y1 - 1978/8/15

N2 - Dialkylboranes such as disiamylborane, dicyclohexylborane and 9-borabicyclo[3.3.1]nonane add cleanly to vinyltrimethylsilane (I) with high regiospecificity (≥ 95%) to give the corresponding β-silylethylboranes, valuable intermediates in the synthesis of functionalized organosilanes. Oxidation of these adducts provides a convenient, high-yield route to 2-trimethylsilylethanol (IIβ). Reduction of acetyltrimethylsilane (IX) with borane-tetrahydrofuran provides a simple route to the isomeric 1-trimethylsilylethanol (IIα). These new developments illustrate the utility of borane reagents in the regiospecific syntheses of trimethylsilylethanols (II).

AB - Dialkylboranes such as disiamylborane, dicyclohexylborane and 9-borabicyclo[3.3.1]nonane add cleanly to vinyltrimethylsilane (I) with high regiospecificity (≥ 95%) to give the corresponding β-silylethylboranes, valuable intermediates in the synthesis of functionalized organosilanes. Oxidation of these adducts provides a convenient, high-yield route to 2-trimethylsilylethanol (IIβ). Reduction of acetyltrimethylsilane (IX) with borane-tetrahydrofuran provides a simple route to the isomeric 1-trimethylsilylethanol (IIα). These new developments illustrate the utility of borane reagents in the regiospecific syntheses of trimethylsilylethanols (II).

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Vinylmetalloids. II. The high regioselectivity of dialkylboranes in the hydroboration of vinyltrimethylsilane

Abstract

Bibliographical note

Funding

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