A new catalytic route to borylgermyl-substituted buta-1,3-dienes

•An effective catalytic method for the synthesis of borylgermyl-substituted buta-1,3-dienes is proposed.•New borylgermylsubstituted buta-1,3-dienes were synthesized and fully characterized spectrally.•The mechanism of co-dimerization reaction was proposed on the basis of DFT calculations.•The activation energy, determined experimentally, is in agreement with the DFT studies.

The [Ru(CO)ClH(PCy3)2] catalyzed reaction of terminal germyl-substituted alkynes with vinylboronates gives borylgermyl-substituted buta-1,3-dienes as products with high stereo- and regioselectivity. The process that proceeds via direct activation of the Csp-H bond in the germylalkyne, is a very effective and easy tool for the synthesis of unique borylgermylated alkynes. Eight new compounds were synthesized and fully characterized spectrally. We also determined the mechanism of the process on the basis of stoichiometric reactions, kinetic measurements and DFT calculations.

Graphical abstractThe [Ru(CO)ClH(PCy3)2] catalyzed reaction of terminal germyl-substituted alkynes with vinylboronates gives borylgermyl-substituted buta-1,3-dienes as products with high stereo- and regioselectivity. The process that proceeds via direct activation of the Csp-H bond in the germylalkyne, is a very effective and easy tool for the synthesis of unique borylgermylated alkynes. The mechanism of the process was determined on the basis of stoichiometric reactions, kinetic measurements and DFT calculations.Figure optionsDownload full-size imageDownload as PowerPoint slide