Alkene-Carbene Isomerization induced by Borane: Access to an Asymmetrical Diborene

Wei Lu; Yongxin Li; Rakesh Ganguly; Rei Kinjo

doi:10.1021/jacs.7b02251

Alkene-Carbene Isomerization induced by Borane: Access to an Asymmetrical Diborene

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

^*Corresponding author for this work

Nanyang Technological University

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

64 Citations (Scopus)

Abstract

A 2,3-dihydro-1H-1,2-azaborole derivative 2 was converted to a cyclic (alkyl) (amino)carbene (cAAC) via 1,2-hydrogen migration triggered by boranes to afford cAAC-borane adducts. This procedure allowed us to develop an asymmetrical diborene cAAC·(Br)B=B(Br)·IDip 6, which was isolated and fully characterized. The ¹¹ B NMR spectrum, X-ray diffraction analysis and computational studies indicate that π-electrons on the central B ₂ moiety in 6 are unequivalently distributed, and thus polarized. A complete scission of the B=B double bond in 6 was achieved by the treatment with an isonitrile, which led to the formation of a base-stabilized B,N-containing methylenecyclopropane 7.

Original language	English
Pages (from-to)	5047-5050
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	14
DOIs	https://doi.org/10.1021/jacs.7b02251
Publication status	Published - Apr 12 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b02251

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abstract = " A 2,3-dihydro-1H-1,2-azaborole derivative 2 was converted to a cyclic (alkyl) (amino)carbene (cAAC) via 1,2-hydrogen migration triggered by boranes to afford cAAC-borane adducts. This procedure allowed us to develop an asymmetrical diborene cAAC·(Br)B=B(Br)·IDip 6, which was isolated and fully characterized. The 11 B NMR spectrum, X-ray diffraction analysis and computational studies indicate that π-electrons on the central B 2 moiety in 6 are unequivalently distributed, and thus polarized. A complete scission of the B=B double bond in 6 was achieved by the treatment with an isonitrile, which led to the formation of a base-stabilized B,N-containing methylenecyclopropane 7.",

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AU - Kinjo, Rei

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N2 - A 2,3-dihydro-1H-1,2-azaborole derivative 2 was converted to a cyclic (alkyl) (amino)carbene (cAAC) via 1,2-hydrogen migration triggered by boranes to afford cAAC-borane adducts. This procedure allowed us to develop an asymmetrical diborene cAAC·(Br)B=B(Br)·IDip 6, which was isolated and fully characterized. The 11 B NMR spectrum, X-ray diffraction analysis and computational studies indicate that π-electrons on the central B 2 moiety in 6 are unequivalently distributed, and thus polarized. A complete scission of the B=B double bond in 6 was achieved by the treatment with an isonitrile, which led to the formation of a base-stabilized B,N-containing methylenecyclopropane 7.

AB - A 2,3-dihydro-1H-1,2-azaborole derivative 2 was converted to a cyclic (alkyl) (amino)carbene (cAAC) via 1,2-hydrogen migration triggered by boranes to afford cAAC-borane adducts. This procedure allowed us to develop an asymmetrical diborene cAAC·(Br)B=B(Br)·IDip 6, which was isolated and fully characterized. The 11 B NMR spectrum, X-ray diffraction analysis and computational studies indicate that π-electrons on the central B 2 moiety in 6 are unequivalently distributed, and thus polarized. A complete scission of the B=B double bond in 6 was achieved by the treatment with an isonitrile, which led to the formation of a base-stabilized B,N-containing methylenecyclopropane 7.

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Alkene-Carbene Isomerization induced by Borane: Access to an Asymmetrical Diborene

Abstract

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