α-C–H difluoroalkylation of alkyl sulfoxides via intermolecular Pummerer reaction
Literature Information
Publication Date
2021-01-22
DOI
10.1039/D0QO01513J
Impact Factor
5.281
Authors
Xin Huang, Weizhao Zhao, Yuchen Liang, Minghui Wang, Yaling Zhan, Yage Zhang, Lichun Kong, Zhi-Xiang Wang, Bo Peng
View Original
Abstract
Pummerer reaction is a well-known protocol for α-functionalization of alkyl sulfoxides. However, in contrast to the progress in developing intramolecular variants, the development of intermolecular Pummerer-type C–C coupling reactions has lagged with limited success, which relies heavily on the use of bases and/or Lewis acids. Herein, we demonstrate that difluoroenol silyl ether is an effective C-nucleophile to perform intermolecular Pummerer reaction without any additives, leading to highly selective α-C–H difluoroalkylation of a wide variety of alkyl sulfoxides including drug analogues and natural product derivatives. Mechanistic studies reveal that the success of the reaction originates from the electron withdrawing effect of fluorine in difluoroenol silyl ether which gives it the ability to distinguish different S(IV) species.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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![[2',6'-bis(propan-2-yloxy)-[1,1'-biphenyl]-3-yl]dicyclohexylphosphane structure](https://static.chemtradehub.com/structs/787/787618-22-8-dda2.webp "[2',6'-bis(propan-2-yloxy)-[1,1'-biphenyl]-3-yl]dicyclohexylphosphane structure")
[2',6'-bis(propan-2-yloxy)-[1,1'-biphenyl]-3-yl]dicyclohexylphosphane
CAS Number:
787618-22-8
Molecular Formula:
C30H43O2P
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