Direct, Sequential, and Stereoselective Alkynylation of C,C-Dibromophosphaalkenes
2016 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 30, 10614-10619 p.Article in journal (Refereed) Published
The first direct alkynylation of C,C-dibromophosphaalkenes by a reaction with sulfonylacetylenes is reported. Alkynylation proceeds selectively in the trans position relative to the P substituent to afford bromoethynylphosphaalkenes. Owing to the absence of transition metals in the procedure, the previously observed conversion of dibromophosphaalkenes into phosphaalkynes through the phosphorus analog of the Fritsch-Buttenberg-Wiechell rearrangement is thus suppressed. The bromoethynylphosphaalkenes can subsequently be converted to C,C-diacetylenic, cross-conjugated phosphaalkenes by following a Sonogashira coupling protocol in good overall yields. By using the newly described method, full control over the stereochemistry at the P=C double bond is achieved. The substrate scope of this reaction is demonstrated for different dibromophosphaalkenes as well as different sulfonylacetylenes.
Place, publisher, year, edition, pages
2016. Vol. 22, no 30, 10614-10619 p.
alkynylation, cross-conjugation, phosphaalkenes, Sonogashira coupling, sulfonyl coupling
IdentifiersURN: urn:nbn:se:uu:diva-302705DOI: 10.1002/chem.201601955ISI: 000380273300043PubMedID: 27310813OAI: oai:DiVA.org:uu-302705DiVA: diva2:967390
FunderSwedish Research CouncilCarl Tryggers foundation