1404075-64-4Relevant academic research and scientific papers
Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism
Baran, Phil S.,Blackmond, Donna G.,Gao, Yang,Hadt, Ryan G.,Hao, Wei,Hill, David E.,McNicholas, Brendon J.,Reisman, Sarah E.,Vantourout, Julien C.
, p. 9478 - 9488 (2021/07/19)
One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.
Convergent synthesis of conjugated 1,2-disubstituted E-allylic alcohols from two aldehydes and methylenetriphenylphosphorane
Hodgson, David M.,Persaud, Rosanne S. D.
supporting information, p. 7949 - 7951 (2013/06/27)
β-Lithiooxyphosphonium ylides, made in situ from an aldehyde and methylenetriphenylphosphorane, react with a second aldehyde to form E-allylic alcohols. α-Branching and α,β-unsaturation in the second aldehyde, together with the lack of further substitution on the phosphorane carbon play important roles in selectivity. A range of these aldehydes, in addition to aromatic aldehydes as the second aldehyde also provided synthetically useful access to E-allylic alcohols.
