52829-83-1Relevant articles and documents
From Dimethylamine to Pyrrolidine: The Development of an Improved Nickel Pincer Complex for Cross-Coupling of Nonactivated Secondary Alkyl Halides
Perez Garcia, Pablo M.,Di Franco, Thomas,Epenoy, Alexandre,Scopelliti, Rosario,Hu, Xile
, p. 258 - 261 (2016/01/12)
Replacement of a dimethyl amino group of the amidobis(amine) nickel(II) pincer complex (1), [(MeN2N)Ni-Cl], by a pyrrolidino group resulted in a new nickel(II) pincer complex (2), [(PyrNMeNN)Ni-Cl]. Complex 2 is an efficient catalyst for Kumada and Suzuki-Miyaura cross-coupling of nonactivated secondary alkyl halides, while complex 1 is largely inactive. The significant activity difference is tentatively attributed to a minimal structural difference, which leads to a more hemilabile ligand.
Lewis Acid Mediated Reactions of Organocopper Reagents. Entrainment in the Conjugate Addition to α,β-Unsaturated Ketones, Esters, and Acids via the RCu*BF3 System
Yamamoto, Yoshinori,Yamamoto, Sinichi,Yatagai, Hidetaka,Ishihara, Yuji,Maruyama, Kazuhiro
, p. 119 - 126 (2007/10/02)
Lewis acid mediated reactions of organocopper reagents with various kinds of α,β-unsaturated carbonyl derivatives are described.RCu*BF3, as well as RCu-other Lewis acid systems, is useful for the conjugate addition to the α,β-unsaturated ketones and esters, whose double bonds are sterically crowded.Certain α,β-unsaturated carboxylic acids also undergo a 1,4-addition through this reagent.Methyl sorbate undergos a 1,4-addition via BuCu*BF3, while undergoing a 1,6-α,δ-addition via Bu2CuLi.BuCu*BF3 reacts more readily with an aldehyde than with a ketone; the degree of chemoselectivity is greater than that of Bu2CuLi, BuLi, or BuMgBr.The R2CuLi-BF3 system is useful for the double alkylation of α,β-unsaturated esters at the β-position and the carbonyl center.Stereochemical aspects of these new copper reagents are also reported.
