Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation

Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation

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 reagen...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-09, Vol.53 (37), p.9851
Hauptverfasser: Gianatassio, Ryan, Kawamura, Shuhei, Eprile, Cecil L, Foo, Klement, Ge, Jason, Burns, Aaron C, Collins, Michael R, Baran, Phil S
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container_issue 37
container_start_page 9851
container_title Angewandte Chemie International Edition
container_volume 53
creator Gianatassio, Ryan
Kawamura, Shuhei
Eprile, Cecil L
Foo, Klement
Ge, Jason
Burns, Aaron C
Collins, Michael R
Baran, Phil S
description 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.
doi_str_mv 10.1002/anie.201406622
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title Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation
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