24374-32-1Relevant articles and documents
Copper-Catalyzed C(sp3)?H Amidation: Sterically Driven Primary and Secondary C?H Site-Selectivity
Bakhoda, Abolghasem (Gus),Jiang, Quan,Badiei, Yosra M.,Bertke, Jeffery A.,Cundari, Thomas R.,Warren, Timothy H.
supporting information, p. 3421 - 3425 (2019/02/14)
Undirected C(sp3)?H functionalization reactions often follow site-selectivity patterns that mirror the corresponding C?H bond dissociation energies (BDEs). This often results in the functionalization of weaker tertiary C?H bonds in the presence of stronger secondary and primary bonds. An important, contemporary challenge is the development of catalyst systems capable of selectively functionalizing stronger primary and secondary C?H bonds over tertiary and benzylic C?H sites. Herein, we report a Cu catalyst that exhibits a high degree of primary and secondary over tertiary C?H bond selectivity in the amidation of linear and cyclic hydrocarbons with aroyl azides ArC(O)N3. Mechanistic and DFT studies indicate that C?H amidation involves H-atom abstraction from R-H substrates by nitrene intermediates [Cu](κ2-N,O-NC(O)Ar) to provide carbon-based radicals R. and copper(II)amide intermediates [CuII]-NHC(O)Ar that subsequently capture radicals R. to form products R-NHC(O)Ar. These studies reveal important catalyst features required to achieve primary and secondary C?H amidation selectivity in the absence of directing groups.
Inter- and intramolecular hydroamination of unactivated alkenes catalysed by a combination of copper and silver salts: The unveiling of a Bronstedt acid catalysis
Michon, Christophe,Medina, Florian,Capet, Frederic,Roussel, Pascal,Agbossou-Niedercorn, Francine
supporting information; experimental part, p. 3293 - 3305 (2011/02/23)
The combined use of a copper halide, a silver salt and a phosphane ligand was applied for the catalysis of inter- and intramolecular hydroamination of alkenes. The reactions of unactivated olefins with nitrogen substrates were investigated. Mechanistic investigations demonstrated that the catalytic system generated a Bronsted acid which appeared to be the prominent catalytic species. Copyright
Highly efficient and reusable ionic liquids for the catalyzed hydroamination of alkenes with sulfonamides, carbamates, and carboxamides
Yang, Lei,Xu, Li-Wen,Xia, Chun-Gu
experimental part, p. 1969 - 1974 (2009/12/26)
SO3H-Functionalized ionic liquids were found to be efficient and reusable catalysts in the hydroamination of sulfonamides, carboxamides, p-nitroaniline and carbamates with nonactivated alkenes. The hydroamination could be performed on a large scale and the acidic ionic liquid catalyst could be reused successfully. Georg Thieme Verlag Stuttgart.
