Nickel/Brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides

Abstract

While chiral allylic organophosphorus compounds are widely utilized in asymmetric catalysis and bioactive molecules, their synthetic methods are still very limited. We report the development of an asymmetric nickel/brønsted acid...

Nickel/Brønsted acid dual-catalyzed regioselective C–H bond allylation of phenols with 1,3-dienes

“…15 Therefore, the development of new catalytic systems for the site-selective C-H bond allylation of phenols with 1,3-dienes is desirable. As a continuation of our previous studies on nickel/ Brønsted acid dual-catalyzed regioselective allylation of N-H 16 and P-H bonds, 17 we speculated that the allylation of phenols will be achieved in an analogous dual catalytic system. Herein, we describe the successful nickel/Brønsted acid dual-catalyzed regioselective allylation of phenols (Fig.…”

Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes and mechanistic studies

“…However, the enantioselective reactions were achieved with limited success. 5 In addition, the control of P -chirality was much more challenging than carbon chiralities as exemplified by Leung’s, 6 Dong’s, 7 Wang’s 8 and Yin's 9 studies, which achieved excellent enantioselectivities of carbon stereocenters but suffered from low d.r. when racemic secondary phosphine oxides were used.…”

Nickel-catalyzed regio- and enantio-selective Markovnikov hydromonofluoroalkylation of 1,3-dienes

“…10 Over the past few years, various highly enantioselective protocols have been used: hydroamination, 11 hydroalkylation, 12 hydroarylation, 13 and hydrosulfonylation, 14 among others. 15 Despite the advances made, these reactions mainly rely on using chiral precious metal Pd and Rh catalysts. Since the landmark work of the Zhou group in 2018, 12 c the use of earth-abundant and low-cost chiral Ni catalysts for developing the asymmetric hydrofunctionalization of acyclic 1,3-dienes has gained increasing attention.…”