Azaborabutadienes: Synthesis by Metal-Free Carboboration of Nitriles and Utility as Building Blocks for B,N-Heterocycles

Lingbing Kong; Wei Lu; Yongxin Li; Rakesh Ganguly; Rei Kinjo

doi:10.1002/anie.201608994

Azaborabutadienes: Synthesis by Metal-Free Carboboration of Nitriles and Utility as Building Blocks for B,N-Heterocycles

Lingbing Kong, Wei Lu, Yongxin Li, Rakesh Ganguly, Rei Kinjo^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

Metal-free regioselective carboboration of arylnitriles with L₂PhB: (1: L=oxazol-2-ylidene) catalyzed by Et₃B afforded the unprecedented acyclic 2-aza-4-borabutadienes 2, thus demonstrating a new strategy to construct a B,C,N-mixed π-system involving B=C and C=N bonds. Thermal isomerization of 2 gave C-borylimines (3), and diverse reactivity of 2 a towards several substrates, such as H⁺, F⁺, O₂, S, Se, and isonitriles, allowed construction of boron-containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.

Original language	English
Pages (from-to)	14718-14722
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	47
DOIs	https://doi.org/10.1002/anie.201608994
Publication status	Published - Nov 14 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

boron
carboboration
heterocycles
multiple bonds
structure elucidation

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10.1002/anie.201608994

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title = "Azaborabutadienes: Synthesis by Metal-Free Carboboration of Nitriles and Utility as Building Blocks for B,N-Heterocycles",

abstract = "Metal-free regioselective carboboration of arylnitriles with L2PhB: (1: L=oxazol-2-ylidene) catalyzed by Et3B afforded the unprecedented acyclic 2-aza-4-borabutadienes 2, thus demonstrating a new strategy to construct a B,C,N-mixed π-system involving B=C and C=N bonds. Thermal isomerization of 2 gave C-borylimines (3), and diverse reactivity of 2 a towards several substrates, such as H+, F+, O2, S, Se, and isonitriles, allowed construction of boron-containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.",

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author = "Lingbing Kong and Wei Lu and Yongxin Li and Rakesh Ganguly and Rei Kinjo",

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doi = "10.1002/anie.201608994",

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AU - Kong, Lingbing

AU - Lu, Wei

AU - Li, Yongxin

AU - Ganguly, Rakesh

AU - Kinjo, Rei

PY - 2016/11/14

Y1 - 2016/11/14

N2 - Metal-free regioselective carboboration of arylnitriles with L2PhB: (1: L=oxazol-2-ylidene) catalyzed by Et3B afforded the unprecedented acyclic 2-aza-4-borabutadienes 2, thus demonstrating a new strategy to construct a B,C,N-mixed π-system involving B=C and C=N bonds. Thermal isomerization of 2 gave C-borylimines (3), and diverse reactivity of 2 a towards several substrates, such as H+, F+, O2, S, Se, and isonitriles, allowed construction of boron-containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.

AB - Metal-free regioselective carboboration of arylnitriles with L2PhB: (1: L=oxazol-2-ylidene) catalyzed by Et3B afforded the unprecedented acyclic 2-aza-4-borabutadienes 2, thus demonstrating a new strategy to construct a B,C,N-mixed π-system involving B=C and C=N bonds. Thermal isomerization of 2 gave C-borylimines (3), and diverse reactivity of 2 a towards several substrates, such as H+, F+, O2, S, Se, and isonitriles, allowed construction of boron-containing heterocycles with various ring sizes, thus illustrating the utility of 2 as a synthetic building block.

KW - boron

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KW - multiple bonds

KW - structure elucidation

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Azaborabutadienes: Synthesis by Metal-Free Carboboration of Nitriles and Utility as Building Blocks for B,N-Heterocycles

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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