- Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents
-
A cobalt-catalyzed cross-coupling between 3- and 4-iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)-preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates. Scaffold synthesis: A cobalt-catalyzed cross-coupling between iodopiperidines and Grignard reagents is reported (see scheme; PG=protecting group). A large variety of 3- and 4-substituted piperidines were synthesized and the method was applied to a short synthesis of (±)-preclamol. This work constitutes one of the rare examples of cross-couplings involving 3-halogeno piperidines.
- Gonnard, Laurine,Gurinot, Amandine,Cossy, Janine
-
p. 12797 - 12803
(2015/09/01)
-
- Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with grignard reagents
-
Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.
- Barr, Baptiste,Gonnard, Laurine,Campagne, Rmy,Reymond, Sbastien,Marin, Julien,Ciapetti, Paola,Brellier, Marie,Gurinot, Amandine,Cossy, Janine
-
p. 6160 - 6163
(2015/01/16)
-
- Selective C-F bond activation: Substitution of unactivated alkyl fluorides using YbI3
-
F makes the break: The carbon-fluorine single bond is quite strong, thus making aliphatic C-F bond scission unusually challenging. A new methodology utilizing YbI3 leads to the conversion of a C-F bond into a C-I bond, and is compatible with various functional groups. The reaction is exceptionally selective towards alkyl fluorides and proceeds under mild conditions. Copyright
- Traeff, Annika M.,Janjetovic, Mario,Ta, Linda,Hilmersson, Goeran
-
supporting information
p. 12073 - 12076
(2013/12/04)
-