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Ring expansion reactions of pentaphenylborole with dipolar molecules as a route to seven-membered boron heterocycles. | LitMetric

Ring expansion reactions of pentaphenylborole with dipolar molecules as a route to seven-membered boron heterocycles.

Inorg Chem

Baylor University, Department of Chemistry and Biochemistry, One Bear Place 97348, Waco, Texas 76798, United States.

Published: February 2015

AI Article Synopsis

Article Abstract

Reactions of pentaphenylborole with isocyanates, benzophenone, and benzaldehyde produced new seven-membered heterocycles in high yields. For 1-adamantyl isocyanate, a BNC5 heterocycle was obtained from the insertion of the C-N moiety into the five-membered borole, whereas for 4-methoxyphenyl isocyanate, a BOC5 heterocycle was generated from the insertion of the C-O unit. These reactions are believed to occur via a mechanism wherein coordination of the nucleophile to the borole (1-adamantyl, N-coordination or O-coordination for 4-methoxyphenyl) is followed by ring expansion to afford the observed seven-membered heterocycles. The selectivity to form B-O- or B-N-containing heterocycles is based on the polarization of the isocyanate implying tunable reactivity for the system. Having observed that isocyanates react as 1,2-dipoles with pentaphenylborole, we examined benzophenone and benzaldehyde, which both reacted to insert C-O units into the ring. This represents a new efficient method for preparing rare seven-membered boracycles.

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Source
http://dx.doi.org/10.1021/ic502784dDOI Listing

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