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Issue 24, 2010
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Borylnitrenes: electrophilic reactive intermediates with high reactivity towards C–H bonds

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Abstract

Borylnitrenes (catBN 3a and pinBN 3b; cat = catecholato, pin = pinacolato) are reactive intermediates that show high tendency towards insertion into the C–H bonds of unactivated hydrocarbons. The present article summarizes the matrix isolation investigations that were aimed at identifying, characterizing and investigating the chemical behaviour of 3a by spectroscopic means, and of the experiments in solution and in the gas phase that were performed with 3b. Comparison with the reactivity reported for difluorovinylidene 1a in solid argon indicates that 3a shows by and large similar reactivity, but only after photochemical excitation. The derivative 3b inserts into the C–H bonds of hydrocarbon solvents in high yields and thus allows the formation of primary amines, secondary amines, or amides from “unreactive” hydrocarbons. It can also be used for generation of methylamine or methylamide from methane in the gas phase at room temperature. Remaining challenges in the chemistry of borylnitrenes are briefly summarized.

Graphical abstract: Borylnitrenes: electrophilic reactive intermediates with high reactivity towards C–H bonds

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Article information


Submitted
11 May 2010
Accepted
19 Aug 2010
First published
07 Oct 2010

Org. Biomol. Chem., 2010,8, 5477-5482
Article type
Emerging Area

Borylnitrenes: electrophilic reactive intermediates with high reactivity towards C–H bonds

H. F. Bettinger and M. Filthaus, Org. Biomol. Chem., 2010, 8, 5477
DOI: 10.1039/C0OB00107D

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