Angewandte Chemie - International Edition

, volume 54 , issue 19 , pages 5632-5635

Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions

Shengtao Ding ¹

Li Juan Song ²

Yong Wang ¹

Xinhao Zhang ²

Lung Wa Chung ³

Yun-Dong Wu ²

J. Q. Sun ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China) |

Laboratory of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China |

Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (China) |

Publication type: Journal Article

Publication date: 2015-03-17

Wiley

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR: 5.550

CiteScore: 27.6

Impact factor: 16.9

ISSN: 14337851, 15213773

DOI: 10.1002/anie.201500372

Copy DOI

PubMed ID: 25784284

General Chemistry

Catalysis

Abstract

A general and mild hydrosilylation of thioalkynes is described. With the cationic catalyst [Cp*Ru(MeCN)3 ](+) and the bulky silane (TMSO)3 SiH, a range of thioalkynes underwent smooth hydrosilylation at room temperature with excellent α regioselectivity and syn stereoselectivity. DFT calculations provided important insight into the mechanism, particularly the unusual syn selectivity with the [Cp*Ru(MeCN)3 ](+) catalyst. The sulfenyl group in the substrates was found to provide important chelation stabilization to direct the reaction through a new mechanistic pathway.

Found

Top-30

Journals

	1 2 3 4 5 6 7 8 9
Journal of Organic Chemistry	Journal of Organic Chemistry, 9, 9% Journal of Organic Chemistry 9 publications, 9%
Organic Letters	Organic Letters, 9, 9% Organic Letters 9 publications, 9%
Journal of the American Chemical Society	Journal of the American Chemical Society, 9, 9% Journal of the American Chemical Society 9 publications, 9%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 7, 7% Angewandte Chemie - International Edition 7 publications, 7%
Angewandte Chemie	Angewandte Chemie, 7, 7% Angewandte Chemie 7 publications, 7%
Nature Communications	Nature Communications, 5, 5% Nature Communications 5 publications, 5%
Chemistry - A European Journal	Chemistry - A European Journal, 5, 5% Chemistry - A European Journal 5 publications, 5%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 5, 5% European Journal of Organic Chemistry 5 publications, 5%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 5, 5% Organic Chemistry Frontiers 5 publications, 5%
Chemical Communications	Chemical Communications, 5, 5% Chemical Communications 5 publications, 5%
Bulletin of the Chemical Society of Japan	Bulletin of the Chemical Society of Japan, 2, 2% Bulletin of the Chemical Society of Japan 2 publications, 2%
ACS Catalysis	ACS Catalysis, 2, 2% ACS Catalysis 2 publications, 2%
Organometallics	Organometallics, 2, 2% Organometallics 2 publications, 2%
Chemical Science	Chemical Science, 2, 2% Chemical Science 2 publications, 2%
Communications Chemistry	Communications Chemistry, 1, 1% Communications Chemistry 1 publication, 1%
Computational and Theoretical Chemistry	Computational and Theoretical Chemistry, 1, 1% Computational and Theoretical Chemistry 1 publication, 1%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 1% Coordination Chemistry Reviews 1 publication, 1%
Tetrahedron Letters	Tetrahedron Letters, 1, 1% Tetrahedron Letters 1 publication, 1%
iScience	iScience, 1, 1% iScience 1 publication, 1%
ChemInform	ChemInform, 1, 1% ChemInform 1 publication, 1%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 1% Asian Journal of Organic Chemistry 1 publication, 1%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 1, 1% Chemistry - An Asian Journal 1 publication, 1%
ChemCatChem	ChemCatChem, 1, 1% ChemCatChem 1 publication, 1%
European Journal of Inorganic Chemistry	European Journal of Inorganic Chemistry, 1, 1% European Journal of Inorganic Chemistry 1 publication, 1%
Accounts of Chemical Research	Accounts of Chemical Research, 1, 1% Accounts of Chemical Research 1 publication, 1%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 1% Organic and Biomolecular Chemistry 1 publication, 1%
Synthesis	Synthesis, 1, 1% Synthesis 1 publication, 1%
Chem	Chem, 1, 1% Chem 1 publication, 1%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 1, 1% Organic Reaction Mechanisms 1 publication, 1%
	1 2 3 4 5 6 7 8 9

Publishers

	5 10 15 20 25 30 35
American Chemical Society (ACS)	American Chemical Society (ACS), 32, 32% American Chemical Society (ACS) 32 publications, 32%
Wiley	Wiley, 32, 32% Wiley 32 publications, 32%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 15, 15% Royal Society of Chemistry (RSC) 15 publications, 15%
Elsevier	Elsevier, 11, 11% Elsevier 11 publications, 11%
Springer Nature	Springer Nature, 6, 6% Springer Nature 6 publications, 6%
Oxford University Press	Oxford University Press, 2, 2% Oxford University Press 2 publications, 2%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 1% Georg Thieme Verlag KG 1 publication, 1%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1%
	5 10 15 20 25 30 35

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

100

Cite this

GOST |

Cite this

GOST Copy

Ding S. et al. Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 19. pp. 5632-5635.

GOST all authors (up to 50) Copy

Ding S., Song L. J., Wang Y., Zhang X., Chung L. W., Wu Y., Sun J. Q. Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 19. pp. 5632-5635.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1002/anie.201500372

UR - https://doi.org/10.1002/anie.201500372

TI - Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions

T2 - Angewandte Chemie - International Edition

AU - Ding, Shengtao

AU - Song, Li Juan

AU - Wang, Yong

AU - Zhang, Xinhao

AU - Chung, Lung Wa

AU - Wu, Yun-Dong

AU - Sun, J. Q.

PY - 2015

DA - 2015/03/17

PB - Wiley

SP - 5632-5635

IS - 19

VL - 54

PMID - 25784284

SN - 1433-7851

SN - 1521-3773

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2015_Ding,

author = {Shengtao Ding and Li Juan Song and Yong Wang and Xinhao Zhang and Lung Wa Chung and Yun-Dong Wu and J. Q. Sun},

title = {Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions},

journal = {Angewandte Chemie - International Edition},

year = {2015},

volume = {54},

publisher = {Wiley},

month = {mar},

url = {https://doi.org/10.1002/anie.201500372},

number = {19},

pages = {5632--5635},

doi = {10.1002/anie.201500372}

}

MLA

Cite this

MLA Copy

Ding, Shengtao, et al. “Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions.” Angewandte Chemie - International Edition, vol. 54, no. 19, Mar. 2015, pp. 5632-5635. https://doi.org/10.1002/anie.201500372.

Publisher

Wiley

Journal

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR

5.550

CiteScore

27.6

Impact factor

16.9

ISSN

14337851 (Print)

15213773 (Electronic)