In:
Angewandte Chemie, Wiley, Vol. 134, No. 34 ( 2022-08-22)
Abstract:
Being isoelectronic with alkynes, iminoboranes with a polar B≡N triple bond have been exclusively investigated as a potent 1,2‐dipole in synthetic chemistry. Herein, we disclose the unprecedented reactivity of aryliminoboranes via the BNCC π conjugation, namely hetero‐enyne behavior. This allows for facile dearomative Diels–Alder‐like reactions of aryliminoboranes with aldehydes. This cycloaddition features mild conditions, is catalyst‐free, and has a broad substrate scope and good functional group tolerance. Kinetic and computational studies reveal its second‐order reaction and concerted cyclization mechanism. This report unveils new synthetic application of iminoboranes beyond their classical reaction patterns.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v134.34
DOI:
10.1002/ange.202205814
Language:
English
Publisher:
Wiley
Publication Date:
2022
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514305-6
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505872-7
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1479266-7
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506259-7
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