A simple synthesis of allylsilanes via tris[(trimethylsilyl)methyl]borane

Wang, Kung K.; Dhumrongvaraporn, Sujitra

doi:10.1016/s0040-4039(00)95897-0

Cited by 17 publications

(1 citation statement)

References 8 publications

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“…They are also versatile reagents in synthetic chemistry [3, 4] and for example, functionalized allylic silanes have been synthesized in high yield from the reaction of tris(trimethylsilyl)methyl borane (Me 3 Si) 3 CBH 2 with alkenyl lithium reagent [4]. However, related heteroleptic systems with differing group 14 groups have received only scant attention [5–7].…”

Section: Introductionmentioning

confidence: 99%

Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including the unexpected formation of arenechromiumtricarbonyldimethylsilanol, (η6-C6H5)Cr(CO)3SiMe2OH

Sharma

Cervantes‐Lee

Pannell

2010

Journal of Organometallic Chemistry

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Treatment of PhMe 2 SiCH 2 GeMe 3 (1) with t-BuLi followed by addition of Me 3 ECl, E = Sn, Pb, results in the formation of phenylsilyl(germyl)stannyl-and phenylsilyl(germyl)plumbyl-methanes, PhMe 2 Si(Me 3 Ge)(EMe 3 )CH, E = Sn (2), Pb (3). The thermal reaction of 1, 2 and 3 with Cr(CO) 6 yields the corresponding aryl-Cr(CO) 3 analogs, {(η 6 -C 6 H 5 )Cr(CO) 3 }Me 2 Si(Me 3 Ge)CH 2 (4) and {(η 6 -C 6 H 5 )Cr(CO) 3 }Me 2 Si(Me 3 Ge)(EMe 3 )CH, E = Sn (5), Pb (6). The thermal treatment of 2 with Cr(CO) 6 in wet THF/di-n-butyl ether mixture results in the formation of the arenechromiumtricarbonyl silanol {(η 6 -C 6 H 5 )Cr(CO) 3 }Me 2 SiOH (7) which exhibits amphiphilic character, forming H-bonded chains in the solid state in a head-to-head arrangement of the areneCr(CO) 3 units.

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Section: Introductionmentioning

confidence: 99%

Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including the unexpected formation of arenechromiumtricarbonyldimethylsilanol, (η6-C6H5)Cr(CO)3SiMe2OH

Sharma

Cervantes‐Lee

Pannell

2010

Journal of Organometallic Chemistry

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Hydroboration

Zaidlewicz

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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The hydroboration reaction and transformations of its organoborane products are described. The mechanism and the chemo‐, regio‐, and stereoselectivity of the hydroboration reaction are presented, as well as the synthesis and characteristics of the most common hydroborating agents. Transformations of organoboranes may involve carbon‐hetero atom bond formation and lead to stereoselective synthesis of organic halides, amines, aziridines, sulfur, selenium, and mercury compounds. Hydroboration‐protonolysis is a nonocatalytic method of cis‐hydrogenation of multiple bonds. Hydroboration‐oxidation is a standard method for cis‐anti‐Markovnikov hydroxylation of multiple bonds. Carbon‐carbon bond formation can be accomplished by transformation of organoboranes through coupling of groups attached to boron, cross‐coupling of organoboranes with organic halides, organoborate rearrangements providing access to alkynes, ( E )‐ and ( Z )‐alkenes, ( E,E )‐, ( E,Z )‐, ( Z,Z )‐dienes, and enynes. Single‐carbon insertion reactions include carbonylation, cyanidation, and the DCME and related reactions. Other reactions include α‐ and β‐alkylation of carbonyl compounds, the addition of alkynyl, alkenyl, and allylic boranes to aldehydes, leading to proparylic alcohols and stereodefined allylic and homoallylic alcohols, boron‐stabilized carbanions, the boron Wittig reaction, and concerted reactions of allylic and vinylic boranes. Contrathermodynamic isomerization of olefins is discussed. The synthesis of boron‐containing polymers and of isotopically labeled compounds is covered. Asymmetric synthesis via chiral organoboranes is covered in detail.

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Hydroboration

Zaidlewicz

2005

Kirk-Othmer Encyclopedia of Chemical Technology

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The hydroboration reaction and transformations of its organoborane products are described. The mechanism and the chemo‐, regio‐, and stereoselectivity of the uncatalyzed and catalyzed hydroboration reaction are presented, as well as the synthesis and characteristics of the most common hydroborating agents. Transformations of organoboranes may involve carbon–heteroatom bond formation and lead to stereoselective synthesis of organic halides, amines, aziridines, sulfur, selenium, mercury, and zinc compounds. Hydroboration–protonolysis is a nonocatalytic method for cis hydrogenation of multiple bonds. Hydroboration–oxidation is a standard method for cis‐anti‐Markovnikov hydroxylation of multiple bonds, whereas the catalyzed hydroboration may lead to Markovnikov hydroxylation. Contrathermodynamic isomerization of olefins is discussed. Carbon–carbon bond formation can be accomplished by transformation of organoboranes through coupling of groups attached to boron, cross‐coupling of organoboranes with organic halides and triflates, organoborate rearrangements providing access to alkynes, dienes, and enynes. Single‐carbon insertion reactions, make possible homologation of organoboranes. Other transformations include α‐alkylation of carbonyl compounds, the boron Wittig reaction, concerted reactions of allylic and vinylic boranes, allylboration, allenylboration and propargylboration of aldehydes leading to stereodefined allylic, homoallylic, and allenyl alcohols. The synthesis of boron‐containing polymers and isotopically labeled compounds is covered. Asymmetric synthesis via chiral organoboranes and stereodirected enolboration–aldolization is described.

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A simple synthesis of allylsilanes via tris[(trimethylsilyl)methyl]borane

Cited by 17 publications

References 8 publications

Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including the unexpected formation of arenechromiumtricarbonyldimethylsilanol, (η6-C6H5)Cr(CO)3SiMe2OH

Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including the unexpected formation of arenechromiumtricarbonyldimethylsilanol, (η6-C6H5)Cr(CO)3SiMe2OH

Hydroboration

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