One pot Suzuki coupling – Wittig olefination reactions

Abstract

Bromoarylcarbaldehydes and bromothienylcarbaldehydes undergo Suzuki cross coupling and Wittig reactions in a one pot procedure to give olefins with extended pi systems. Dihaloarenes can be transformed in a double Wittig – / double Suzuki cross coupling reaction to yield functionalised terphenyls.

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

“…Often, the oxidant of choice is MnO 2 [40,[43][44][45][46][79][80][81][82][83][84][85][86][87][88][89][90][91][92][93][94][95][96][97], although a number of reactions are known where transformations were carried with air oxygen using metals and metal oxides as catalysts [72][73][74][75][76][77][78]. As many Wittig-and HWE reactions tolerate metal catalysts, this allows the running of Wittig/HWE reactions in combination with metal catalyzed cross coupling reactions and olefinations such as Heck [114][115][116][117][118][119][120][121][122][123], Suzuki [111][112][113], Sonogashira [119][120]…”

“…Wittig-and Horner-Wadsworth-Emmons reactions can be combined with C─C-coupling reactions such as Suzuki cross-coupling [111][112][113], Mizoroki-Heck reaction [113][114][115][116][117][118] and Sonogashira-reaction [119]. Initially, it was observed that conjugated phosphoranes were stable under reaction conditions used for Heck-or Suzuki reactions (Scheme 9).…”

Heteroareno-annelated estranes by triene cyclization

“…Potentially, one or more double bonds in the triene system can become part of a heterocycle. Recently, the authors developed a new approach to the synthesis of thienyldienes via a Suzuki coupling-Wittig olefination sequence [14,15]. Therefore, it was expedient to utilize this technique in combination with a subsequent thermal triene cyclization for rapid construction of thienoannelated estranes.…”

Water Compatible Multicomponent Cascade Suzuki/Heck–Aldol, Suzuki–Aldol–Suzuki, and Aldol–Suzuki–Aldol Reactions: An Ecofriendly Paradigm for Multiple CarbonCarbon Bond Formation in One Pot

“…There are a handful of reports for the synthesis of thiophene‐centered biarylchalcones14 through Suzuki‐coupling–Wittig‐olefination reactions,14a direct arylation of thiophene‐containing alkenes,14b and arylation of thiophene carboxaldehyde followed by Aldol condensation;13d however, these methods are plagued by several limitations, such as the requirement for one‐pot two‐step reactions, low selectivity for the product, and longer reaction times. Moreover, heterobiarylcarboxaldehyde,15 a key intermediate for the synthesis of thiophene‐centered biarylchalcones, is usually formed in the presence of expensive ligand, such as dialkylbiphenylphosphinyl,15a,b with a metal catalyst in an organic solvent.…”