4912-92-9Relevant articles and documents
Palladium-catalyzed carbon - Carbon bond-forming 1,2-ligand migration of organoalanes
Fillion, Eric,Carson, Rebekah J.,Trepanier, Vincent E.,Goll, Julie M.,Remorova, Anna A.
, p. 15354 - 15355 (2004)
A one-pot, two-step process that transforms terminal alkynes into ethyl methyl-substituted benzylic quaternary carbon centers is described. (E)-2,2-Disubstituted-1-alkenyldimethylalanes have been shown to participate in 1,2-alkyl migration from aluminum to carbon with concomitant arylation at the 2-position to furnish ethyl methyl-substituted benzylic quaternary carbon centers, when reacted intramolecularly with aryl halides and triflates in the presence of a Pd(0) catalyst. The protocol is initiated with Cp2ZrCl2-catalyzed methylalumination of terminal alkynes followed by palladium-catalyzed intramolecular arylation of the resulting (E)-2,2-disubstituted-1-alkenyldimethylalanes, leading to 1,2-methyl shift from aluminum to carbon. In that sequence, a total of three new C-C single bonds are made, and two of the three alkyl groups on Me3Al transferred to the substrate on vicinal carbons. This method was applied to a variety of substrates, and the mechanism was investigated by deuterium-labeling experiments, which revealed that protodealumination of the final dialkylaluminum triflate or halide intermediates by CH3CN results in the formation of the fourth bond in the course of the transformation. Copyright
Ni-catalysed reductive arylalkylation of unactivated alkenes
Jin, Youxiang,Wang, Chuan
, p. 1780 - 1785 (2019)
In this protocol Ni-catalysed reductive arylalkylation of unactivated alkenes tethered to aryl bromides with primary alkyl bromides has been accomplished, providing a new path to construct diverse benzene-fused carbo- and heterocyclic cores including inda
Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes
He, Jun,Xue, Yuhang,Han, Bo,Zhang, Chunzhu,Wang, You,Zhu, Shaolin
supporting information, p. 2328 - 2332 (2020/01/08)
Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.
Nickel-catalyzed asymmetric intramolecular reductive heck reaction of unactivated alkenes
Yang, Feiyan,Jin, Youxiang,Wang, Chuan
, p. 6989 - 6994 (2019/09/30)
An asymmetric Ni-catalyzed intramolecular reductive Heck reaction of unactivated alkenes tethered to aryl bromides has been accomplished, providing a variety of benzene-fused cyclic compounds bearing a quaternary stereogenic center in good to excellent yi