Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

Jin Zhang; Ying Liu; Qiangqiang Jia; Yue Wang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.0c02410

Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

Jin Zhang, Ying Liu, Qiangqiang Jia, Yue Wang, Yangmin Ma, Michal Szostak

Rutgers Newark, Chemistry

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

18 Scopus citations

Abstract

We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.

Original language	English (US)
Pages (from-to)	6884-6890
Number of pages	7
Journal	Organic letters
Volume	22
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.0c02410
State	Published - Sep 4 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c02410

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title = "Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF",

abstract = "We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent. ",

author = "Jin Zhang and Ying Liu and Qiangqiang Jia and Yue Wang and Yangmin Ma and Michal Szostak",

note = "Funding Information: J.Z. thanks the CSC (No. 201808610096). Support was provided by the Foundation for Young Scholars of SUST (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CHE-1650766). Funding Information: J.Z. thanks the CSC (No. 201808610096). Support was provided by the Foundation for Young Scholars of SUST (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CHE-1650766).",

year = "2020",

month = sep,

day = "4",

doi = "10.1021/acs.orglett.0c02410",

language = "English (US)",

volume = "22",

pages = "6884--6890",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

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TY - JOUR

T1 - Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

AU - Zhang, Jin

AU - Liu, Ying

AU - Jia, Qiangqiang

AU - Wang, Yue

AU - Ma, Yangmin

AU - Szostak, Michal

N1 - Funding Information: J.Z. thanks the CSC (No. 201808610096). Support was provided by the Foundation for Young Scholars of SUST (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CHE-1650766). Funding Information: J.Z. thanks the CSC (No. 201808610096). Support was provided by the Foundation for Young Scholars of SUST (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CHE-1650766).

PY - 2020/9/4

Y1 - 2020/9/4

N2 - We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.

AB - We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.

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U2 - 10.1021/acs.orglett.0c02410

DO - 10.1021/acs.orglett.0c02410

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AN - SCOPUS:85090481185

SN - 1523-7060

VL - 22

SP - 6884

EP - 6890

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

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