Sulfonyl Acetylenes and phosphaalkenes

2016-05-13

Shameem and Keyhans paper got accepted in Chemistry - A European Journal.
CONGRATS !!

Direct, sequential and stereoselective alkynylation of C,C-dibromophosphaalkenes
Muhammad A. Shameem, Keyhan Esfandiarfard, Elisabet Öberg, Sascha Ott,* and Andreas Orthaber


The first direct alkynylation of C,C-dibromo-phosphaalkenes by a reaction with sulfonylacetylenes is reported. Alkynylation proceeds selectively in 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 analogue of the Fritsch-Buttenberg-Wiechell rearrangement is thus suppressed. The bromoethynyl-phosphaalkenes can subsequently be converted to C,C-diacetylenic, cross-conjugated phosphaalkenes 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.

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PhD thesis defense: Brigitta Németh                                                                                  Brigitta Németh defends her PhD thesis, "The birth of the hydrogenase", in Å4101 Ångström Laboratory, November 6 at 9:15 hrs. The opponent is  Dr Mohamed Atta from  iRTSV CEA Grenoble. Thesis is available here: https://www.divaportal.org/smash/get/diva2:1352461/FULLTEXT01.pdf

CAP meeting                                                                                                                      The next CAP meeting is on November 4.