Direct C–S bond formation via C–O bond activation of phenols in a crossover Pd/Cu dual-metal catalysis system

Abstract

A highly effective synthesis of unsymmetrical aryl sulfides was introduced under a dual-metal (Pd/Cu) catalysis system with a high turn-over number.

The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S8

“…On basis of these preliminary studies and previous reports, [21][22][23][24][25][26][27][28] a plausible pathway for the preparation of 2a from (E)-N 0 -benzylideneacetohydrazide is proposed in (Scheme 3). Initially, Ag 2 CO 3 react with 1 to produce the intermediate (A).…”

A review on the latest progress of C‐S cross‐coupling in diaryl sulfide synthesis: Update from 2012 to 2021

“…They treated aryl boronic acid 7 , free phenols 69 , S 8 , and characterized palladium immobilized on nano‐silica based particles named SiO 2 @OL@Pd (II) 70 (Scheme 32). [ 52 ]…”

“…They treated aryl boronic acid 7, free phenols 69, S 8 , and characterized palladium immobilized on nano-silica based particles named SiO 2 @OL@Pd (II) 70 (Scheme 32). [52] In 2018, Zhao et al reported the first palladiumcatalyzed oxidative cross-coupling of arylhydrazines 71 and arene thiols 1 with O 2 oxidant and afforded diaryl sulfides 5 in good to high yields (Scheme 33). [53] S C H E M E 2 8 Nickel-catalyzed Chan-Lam cross-coupling of arylboronic acids with sulfonyl hydrazide S C H E M E 2 7 Nickel-catalyzed cross-coupling of arylboronic acids with thiophenols Betch and coworkers used a decarboxylative palladium-catalyzed reaction between electron-rich 2,6-dialkoxybenzoic acid derivatives 72 and diaryl disulfides 74 in the presence of Pd (CF 3 CO 2 ) 2 and Ag 2 CO 3 in a 65:1 mixture of 1,4-dioxane and tetramethylene sulfoxide (TMSO) (Scheme 34).…”

Recent developments in palladium-catalyzed C–S bond formation

“…With the new Pd-nanoparticle and CuI as the co-catalysts, the crosscoupling reaction of unreactive free-phenols (102) with arylboronic acids (103) performed well under optimized conditions (Scheme 38). 62 The developed catalyst [SiO 2 @OL@Pd] showed ultra-high catalytic activity with TONs up to 19 000. Recycling experiments indicated that the palladium nanoparticle catalyst could be recycled up to five times without any decrease in the activity and regioselectivities.…”