Carbon–carbon bond construction using boronic acids and aryl methyl sulfides: orthogonal reactivity in Suzuki-type couplings

Joel F. Hooper, Rowan D. Young, Indrek Pernik, Andrew S. Weller, Michael C. Willis

Research output: Contribution to journalArticlepeer-review

64 Citations (Scopus)

Abstract

The Rh(I)-catalysed coupling of aryl and alkenyl boronic acids with simple aryl and alkenyl methyl sulfides is reported. The process employs bench-stable Rh(I) precatalysts incorporating small bite-angle chelating phosphine ligands (R2PCH2PR2, R = iPr, Cy), shows good functional group tolerance, and proceeds under mild reaction conditions. Importantly, aryl bromide activating groups are inert to the reaction conditions, allowing selective reaction at either a methyl sulfide or bromide activating group, depending on catalyst (metal) choice. The scope of the coupling reactions, their combination with Rh-catalysed hydroacylation reactions in cascade processes, together with preliminary mechanistic studies, are all documented.
Original languageEnglish
Pages (from-to)1568-1572
Number of pages5
JournalChemical Science
Volume4
Issue number4
DOIs
Publication statusPublished - 2013
Externally publishedYes

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