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Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation
Author(s) -
Gianatassio Ryan,
Kawamura Shuhei,
Eprile Cecil L,
Foo Klement,
Ge Jason,
Burns Aaron C.,
Collins Michael R.,
Baran Phil S.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406622
Subject(s) - reagent , decarboxylation , chemistry , reactivity (psychology) , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS‐Na. The reactivity of six of these salts towards CH functionalization was field‐tested using several different classes of heterocycles.