17936-80-0Relevant academic research and scientific papers
Stepwise trimethylsilyl and trimethylgermyl substitutions at tetraborylmethane
Baum, Zachary J.,Zhang, Jingtao,Morasse, Rick A.L.,Goldberger, Joshua E.
, p. 50 - 56 (2018)
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.
