Stepwise trimethylsilyl and trimethylgermyl substitutions at tetraborylmethane

Add time:07/23/2019    Source:sciencedirect.com

In exploring the suitability of tetraborylmethane precursors as C4− synthons, we have studied the limits of stepwise trimethylsilyl and trimethylgermyl substitutions on tetrakis (1,3-propanediolatoboryl)methane. In contrast to previous reports indicating minimal silylation of tetraborylmethanes, we have shown that organolithium-mediated deborylation-metalation methodologies readily proceed for up to two substitutions. This enables the synthesis of new borylmethane derivatives including (TMS)2CB(pg)2 and (TMG)2CB(pg)2 (pg = 1,3-propanediolate, TMS = trimethylsilyl, TMG = trimethylgermyl). While further base-activated deborylation attempts lead to protodeboronation, limited reactivity, or de-esterification of the boronate ester, increasing the degree of substitution imparts air- and water-stability to the boronate esters.

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