54981-97-4Relevant academic research and scientific papers
Highly nucleophilic Vitamin B12-assisted nickel-catalysed reductive coupling of aryl halides and non-activated alkyl tosylates
Komeyama, Kimihiro,Ohata, Ryo,Kiguchi, Shinnosuke,Osaka, Itaru
supporting information, p. 6401 - 6404 (2017/07/10)
Reductive cross-coupling of aryl halides with ubiquitous alkyl tosylates was developed using a combination of nickel and vitamin B12 (VB12: cyanocobalamin) catalysts. The tosylate was activated by reduced VB12 to form alkyl cobalt(iii), which served as a good alkylating agent for aryl-nickel species, leading to C(sp3)-C(sp2) bond formation.
Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
supporting information; experimental part, p. 6039 - 6048 (2012/06/18)
A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright
Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids
Tsui, Gavin Chit,Menard, Frederic,Lautens, Mark
supporting information; experimental part, p. 2456 - 2459 (2010/07/06)
A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH]2 and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity.
