![(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid structure](https://static.chemtradehub.com/structs/126/1269757-29-0-c552.webp "(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid structure")
(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid
CAS Number:
1269757-29-0
Molecular Formula:
C15H19NO4
Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF3Br
Literature Information
Publication Date
2021-09-13
DOI
10.1039/D1QO01073E
Impact Factor
5.281
Authors
Deqian Peng, Wu Fan, Xueqi Zhao, Wei Chen, Yuan Wen, Li Zhang
View Original
Abstract
We report a mild and efficient hydrotrifluoromethylation of alkenes with bromotrifluoromethane (CF3Br) mediated by zinc and a Brønsted acid. This reaction proceeds well with good functional group compatibility and broad substrate scope. Mechanistic studies indicate that the reaction proceeds through a radical pathway, facilitated through the combination of the zinc metal and a Brønsted acid for the single electron reduction of CF3Br to the CF3 radical. Furthermore, the method readily allows the incorporation of deuterium using deuterated carboxylic acid and D2O.
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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
![(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide structure](https://static.chemtradehub.com/structs/250/2505001-54-5-c1e9.webp "(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide structure")
(2E)-3-(3-Chlorophenyl)-N-{2-[4-(methylsulfonyl)-1-piperazinyl]-2-oxoethyl}acrylamide
CAS Number:
2505001-54-5
Molecular Formula:
C16H20ClN3O4S
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