23975-23-7Relevant academic research and scientific papers
Lithiated sulfoxides: α-Sulfinyl functionalized carbanions
Ludwig, Gerd,Rüffer, Tobias,Hoppe, André,Walther, Till,Lang, Heinrich,Ebbinghaus, Stefan G.,Steinborn, Dirk
, p. 5323 - 5330 (2015)
Reactions of alkyl aryl sulfoxides H-CRR′S(O)Ar with n-BuLi-TMEDA (TMEDA = N,N,N′,N′-tetramethylethylenediamine) afforded α-sulfinyl functionalized alkyl aryl lithium compounds of the type [Li2{CRR′S(O)Ar}2(TMEDA)2] (1, R/
Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy
Parisi, Giovanna,Colella, Marco,Monticelli, Serena,Romanazzi, Giuseppe,Holzer, Wolfgang,Langer, Thierry,Degennaro, Leonardo,Pace, Vittorio,Luisi, Renzo
supporting information, p. 13648 - 13651 (2017/11/06)
The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.
