578714-85-9Relevant 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)
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.
Nazarov cyclization of divinyl and arylvinyl epoxides: Application in the synthesis of resveratrol-based natural products
Sudhakar, Gangarajula,Satish, Kovela
supporting information, p. 6475 - 6480 (2015/04/22)
New variation in the Nazarov cyclization has been developed by preparing divinyl and arylvinyl epoxides as pentadienyl cation precursors for the first time. Highly substituted cyclopentadienes, hydrindienes, and indenes were synthesized to demonstrate the compatibility of this reaction with substrates bearing a variety of substitutions and having different types of epoxides. Application of this method in the synthesis of resveratrol-based natural products was also demonstrated.
Domino electrocyclization/azide-capture/Schmidt rearrangement of dienones: One-step synthesis of dihydropyridones from simple building blocks
Song, Dong,Rostami, Ali,West
, p. 12019 - 12022 (2008/03/17)
Simple 1,4-dien-3-ones undergo Lewis acid-catalyzed Nazarov electrocyclization and intermolecular trapping by various azides to furnish 3,4-dihydropyridin-2-ones in moderate to good yields. The reaction is proposed to proceed via nucleophilic trapping of
Formal intermolecular 4 + 4 approach to cyclooctanoids: 4 + 3 Capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes
Wang, Yong,Schill, Brenden B.,Arif, Atta M.,West
, p. 2747 - 2750 (2007/10/03)
(Matrix presented) Simple 1,4-dien-3-ones and 1,3-dienes react in the presence of BF3·OEt2 via a domino Nazarov electrocyclization/intermolecular [4 + 3]-cycloaddition sequence to furnish keto-bridged cyclooctenes in good yield. Most
