Dearomative triple elementalization of quinolines driven by visible light - Nature Communications

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Dearomative triple elementalization of quinolines driven by visible light - Nature Communications
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New horizons for organoboron and organosilicon chemistry with triple elementalization tokodai_news NatureComms

BuLi, resulted in either no reaction or complex mixtures . These results may be attributed to undesired activation . To overcome this problem, we envisioned that selective excitation ofby irradiation at an optimal wavelength would facilitate selective Si–B bond cleavage under mild conditions. Our time-dependent density functional theory calculations of quinoline and model borate complex, assigned to the HOMO–LUMO transition, shows a red shift from that of quinoline .

Notably, the two stereocenters on boron and silane were formed with complete regio- and diastereoselectivity , as confirmed byFig. 2: UV/vis absorption spectrum of INT-A’ by TDDFT calculations.We surveyed various types of light sources to facilitate the Si–B bond cleavage process and found that the yield ofwas drastically improved to 80% when blue LEDs were used . Importantly, the yield significantly decreased under dark conditions .

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