Lin Shengjia, Wang Lucia, Aminoleslami Negin, Lao Yanting, Yagel Chelsea, Sharma Abhishek
Department of Chemistry and Chemical Biology , Stevens Institute of Technology , Hoboken , NJ 07030 , USA . Email:
Chem Sci. 2019 Mar 21;10(17):4684-4691. doi: 10.1039/c9sc00378a. eCollection 2019 May 7.
Acylboronates represent a very intriguing and rare class of organoboronates. Synthesis of these compounds from readily available substrates under mild conditions and access to novel classes of acylborons has been challenging. We report a novel and concise route to various MIDA acylboronates from terminal alkynes/alkenes or vinyl boronic esters using unsymmetrical geminal diborylalkanes as key intermediates. The high modularity and mild conditions of this strategy allowed a facile access to acylboronates possessing aliphatic, aromatic as well as the rarer heteroaromatic, alkynyl and α,β-unsaturated scaffolds. To the best of our knowledge, this is the first report of chemoselective oxidation of geminal diborons as well as synthesis of an α,β-unsaturated acylboronate.
酰基硼酸酯是一类非常有趣且罕见的有机硼酸酯。在温和条件下从容易获得的底物合成这些化合物以及获得新型酰基硼类化合物一直具有挑战性。我们报道了一种新颖且简洁的路线，以不对称偕二硼基烷烃为关键中间体，从末端炔烃/烯烃或乙烯基硼酸酯合成各种MIDA酰基硼酸酯。该策略的高模块化和温和条件使得能够轻松获得具有脂肪族、芳香族以及更罕见的杂芳香族、炔基和α,β-不饱和骨架的酰基硼酸酯。据我们所知，这是偕二硼化学选择性氧化以及α,β-不饱和酰基硼酸酯合成的首次报道。
