Trifluoromethyl sulfoxides: reagents for metal-free C−H trifluoromethylthiolation
Trifluoromethyl sulfoxides: reagents for metal-free C−H trifluoromethylthiolation
Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C−H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.
arenes, pummerer reaction, reaction mechanisms, sulfoxides, trifluoromethylthiolation
15918-15922
Wang, Dong
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Carlton, C. Grace
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Tayu, Masanori
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McDouall, Joseph J.W.
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Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
15 July 2020
Wang, Dong
8252495a-d031-44fa-9f21-6e8c76164aaa
Carlton, C. Grace
6dafc734-13f2-4afc-b60b-48cfdb7f4022
Tayu, Masanori
bc6b05c3-0ce1-4035-999e-049c9fa0c0ea
McDouall, Joseph J.W.
4ca54dfa-6b19-41d4-b531-a5cf701fdd68
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Wang, Dong, Carlton, C. Grace, Tayu, Masanori, McDouall, Joseph J.W., Perry, Gregory J.P. and Procter, David J.
(2020)
Trifluoromethyl sulfoxides: reagents for metal-free C−H trifluoromethylthiolation.
Angewandte Chemie - International Edition, 59 (37), .
(doi:10.1002/anie.202005531).
Abstract
Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C−H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.
Text
Angew Chem Int Ed - 2020 - Wang - Trifluoromethyl Sulfoxides Reagents for Metal‐Free C H Trifluoromethylthiolation
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Accepted/In Press date: 28 May 2020
Published date: 15 July 2020
Additional Information:
Funding Information:
We thank EPSRC (Postdoctoral Fellowship to D. W.—EP/S014128/1; Established Career Fellowship to D.J.P.—EP/M005062/1) and the University of Manchester (Lectureship to G.J.P.P.) for their generous support.
Keywords:
arenes, pummerer reaction, reaction mechanisms, sulfoxides, trifluoromethylthiolation
Identifiers
Local EPrints ID: 478113
URI: http://eprints.soton.ac.uk/id/eprint/478113
ISSN: 1433-7851
PURE UUID: 524b9511-51ed-4d5d-8b50-afefe74c940c
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Date deposited: 21 Jun 2023 17:09
Last modified: 18 Mar 2024 04:11
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Contributors
Author:
Dong Wang
Author:
C. Grace Carlton
Author:
Masanori Tayu
Author:
Joseph J.W. McDouall
Author:
Gregory J.P. Perry
Author:
David J. Procter
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