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Direct, Sequential, and Stereoselective Alkynylation of C,C-Dibromophosphaalkenes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
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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
Abstract [en]

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.
Keyword [en]
alkynylation, cross-conjugation, phosphaalkenes, Sonogashira coupling, sulfonyl coupling
National Category
Inorganic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-302705DOI: 10.1002/chem.201601955ISI: 000380273300043PubMedID: 27310813OAI: oai:DiVA.org:uu-302705DiVA: diva2:967390
Funder
Swedish Research CouncilCarl Tryggers foundation
Available from: 2016-09-08 Created: 2016-09-08 Last updated: 2016-09-08Bibliographically approved

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Shameem, Muhammad A.Esfandiarfard, KeyhanOtt, SaschaOrthaber, Andreas
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