Rhodium-Catalyzed B–H Activation of 1,2-Azaborines: Synthesis and Characterization of BN Isosteres of Stilbenes

来自 ACS

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作者：

Alec，N.，Brown，Lev，N.，Zakharov，Tanya，Mikulas，David，A.

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摘要：

The first example of catalytic B–H activation of azaborines leading to a new family of stilbene derivatives through dehydrogenative borylation is reported. Ten 1,2-azaborine-based BN isosteres of stilbenes have been synthesized using this method, including a BN isostere of a biologically active stilbene. It is demonstrated that BN/CC isosterism in the context of stilbenes can lead to significant changes in the observed photophysical properties such as higher quantum yield and a larger Stokes shift. Direct comparative analysis of BN stilbene 3g and its carbonaceous counterpart 6g is consistent with a stronger charge-transfer character of the excited state exhibited by 3g in which the 1,2-azaborine heterocycle serves as a better electron donor than the corresponding arene.

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关键词：

organo‐boron compounds catalysis, phase‐transfer catalysis optical properties (excluding spectra) (organic substances

DOI：

10.1021/ol501362w

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年份：

2014