Upon their generation from bis-1,3-diynes in the presence of a silver (I) catalyst, aryne species have shown two contrasting reaction profiles toward alkane C�H bonds on the �-carbon of silyl groups . While 1� C�H bonds participate exclusively in a direct C�H insertion process, the corresponding 2o and 3o C�H bonds are subject to hydride transfer to generate products of a formal hydrogenation of the aryne moiety. The electronic and steric effect on the C�H bonds at the �-carbon of the silyl groups can be exploited in aryne-mediated transformations to generate complementary products and these two differnet reaction pathways can be rationalized by the stability of the incipient cabocationic intermediates which is further supported by DFT-calculations.

Formal hydrogenation of arynes with silyl C<sub>�</sub>�H bonds as an active hydride source

248th National Meeting (2014)

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Formal hydrogenation of arynes with silyl C��H bonds as an active hydride source

Formal hydrogenation of arynes with silyl C_��H bonds as an active hydride source