Water-mediated C–H activation of arenes with secure carbene precursors: the reaction and its application

Abstract

A water-mediated C–H activation using sulfoxonium ylides is reported, providing a general, green and step-economic approach to construct a C–C bond and varieties of useful N-heterocycle scaffolds.

Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study

“…It was generally proposed that the cyclic product was formed by the first generation of an acylmethylation intermediate in similar cascade reactions. (Chen et al, 2018;Hu et al, 2018aHu et al, ,b, 2019Liang et al, 2018;Shi et al, 2018;Xiao et al, 2018;Xie et al, 2018bXie et al, , 2019Xie H. et al, 2018;Xu et al, 2018;Zhou et al, 2018;Cai et al, 2019;Chen P. et al, 2019;Cui et al, 2019;Huang et al, 2019;Lai et al, 2019;Liu et al, 2019;Luo et al, 2019;Lv et al, 2019;Nie et al, 2019;Shen et al, 2019;Wu C. et al, 2019;Zhang et al, 2019Zhang et al, , 2020Wu et al, 2020). Further transformations from IM6 were explored theoretically to confirm whether the acylmethylation intermediate (IM8) is key in the formation of 2a (Figure 2).…”

Synthesis of Isoquinolines via Rh(III)‐Catalyzed C−H Annulation of Primary Benzylamines with α‐Cl Ketones

“…Subsequently, the groups of Li's and Cheng's successively reported an alternative synthesis of isoquinolines through Rh(III)‐catalyzed coupling of benzylamines with diazo compounds (Scheme 1b) [8] . Recently, Wu and co‐workers used sulfoxonium ylides as safer alternative coupling partners to diazo compounds in Rh(III)‐catalyzed C−H annulation of benzylamines (Scheme 1c) [9] . However, among these reactions, the coupling partners were currently limited to the sp‐carbon synthons or metal carbine precursors.…”

“…[8] Recently, Wu and co-workers used sulfoxonium ylides as safer alternative coupling partners to diazo compounds in Rh(III)-catalyzed CÀ H annulation of benzylamines (Scheme 1c). [9] However, among these reactions, the coupling partners were currently limited to the sp-carbon synthons or metal carbine precursors. To the best of our knowledge, sp 3 -carbon synthons as coupling reagents have not been reported in the CÀ H functionalization of benzylamines.…”

Rhodium(iii)-catalyzed annulation of enamides with sulfoxonium ylides toward isoquinolines

“…17 Very recently, preparation of isoquinoline derivatives by Rh(III)-catalyzed coupling reaction of benzylamine and sulfoxonium ylides using water as solvent is achieved by Wu and coworkers (Scheme 1c). 18 Enamides are valuable building blocks in organic synthesis having tunable reactivity and potential usage in various transformations. 19 The potential of enamide chemistry has been witnessed by transition-metal-catalyzed coupling reactions.…”