|
|||||
|
|
Simple Sulfinate Synthesis Enables CH Trifluoromethylcyclopropanation |
|
| Authors: | Ryan Gianatassio Dr Shuhei Kawamura Cecil L Eprile Dr Klement Foo Jason Ge Dr Aaron C Burns Dr Michael R Collins Prof?Dr Phil S Baran |
| Institution: | 1. Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA);2. Department of Chemistry, Pfizer Pharmaceuticals, La Jolla Laboratories, 10770 Science Center Drive, La Jolla, CA 92121 (USA) |
| Abstract: | 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 C? H functionalization was field‐tested using several different classes of heterocycles. |
| Keywords: | analogue synthesis bioisosteres C H functionalization heterocycles sulfinate salts |