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Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane
Xia, Yuanzhi1,2; Li, Yahong1,2; Li, Wu2
2008-12-01
Source PublicationJOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume693Issue:25Pages:3722-3728
SubtypeArticle
AbstractThe detailed pathway of the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl( vinyl) silane with borane were studied theoretically by DFT calculations. It is found that the 1,2-hydroboration will occur at the C = C moiety when the alkynyl end is substituted, and give the anti-Markovnikov adduct as a result of steric hindrance. From the 1,2-hydroboration intermediate, the intramolecular 1,1-organoboration is a concerted asynchronous process, in which the, C-Si cleavage precedes 1,2-alkyl migration, with activation energy about 25 kcal/mol. Calculations reveal the electronic property of the substituent at the alkyne end has quite limited effect on the 1,1-organoboration activation energy. The ring constrain is found to influence the weak Si-H-B interactions in the 1-silacyclopent-2-ene product most, and similar C-H-B interactions were predicted for the corresponding carbon analogues. (C) 2008 Elsevier B. V. All rights reserved.
KeywordDft Calculation 1 Si-h-b Interaction 2-hydroboration 1 Mechanism 1-organoboration Energy
WOS HeadingsScience & Technology ; Physical Sciences
WOS KeywordH-B BRIDGES ; RHODIUM-CATALYZED HYDROBORATION ; STEREOSELECTIVE-SYNTHESIS ; SELECTIVE HYDROBORATION ; MARKOVNIKOV HYDROBORATION ; ASYMMETRIC HYDROBORATION ; REDUCTIVE ALKYLATION ; TERMINAL ALKENES ; VINYLSILANES ; OXIDATION
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic
WOS IDWOS:000260758100007
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Document Type期刊论文
Identifierhttp://ir.isl.ac.cn/handle/363002/5833
Collection青海盐湖研究所知识仓储
Affiliation1.Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
2.Chinese Acad Sci, Qinghai Inst Salt Lakes, Xining 810008, Peoples R China
Recommended Citation
GB/T 7714
Xia, Yuanzhi,Li, Yahong,Li, Wu. Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY,2008,693(25):3722-3728.
APA Xia, Yuanzhi,Li, Yahong,&Li, Wu.(2008).Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane.JOURNAL OF ORGANOMETALLIC CHEMISTRY,693(25),3722-3728.
MLA Xia, Yuanzhi,et al."Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane".JOURNAL OF ORGANOMETALLIC CHEMISTRY 693.25(2008):3722-3728.
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