Tandem [4 + 2]/[2 + 2] cycloaddition of o-carboryne with enynes: facile construction of carborane-fused tricyclics

Jie Zhang; Zuowei Xie

doi:10.1039/d0sc07047e

Tandem [4 + 2]/[2 + 2] cycloaddition of o-carboryne with enynes: facile construction of carborane-fused tricyclics

Jie Zhang
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

7 Citations (Scopus)

Abstract

o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. With 1-Li-2-OTf-o-C₂B₁₀H₁₀ as the precursor, o-carboryne undergoes an efficient [4 + 2] cycloaddition with various conjugated enynes, followed by a subsequent [2 + 2] cycloaddition at room temperature, generating a series of carborane-fused tricyclo[6.4.0.0^2,7]dodeca-2,12-dienes in moderate to high isolated yields. This reaction is compatible with many functional groups and has a broad substrate scope. A reactive carborane-fused 1,2-cyclohexadiene intermediate is involved, which is supported by experimental results and DFT calculations. This protocol offers a convenient strategy for the construction of complex carborane-functionalized tricyclics.

Original language	English
Pages (from-to)	5616-5620
Number of pages	5
Journal	Chemical Science
Volume	12
Issue number	15
Early online date	22 Feb 2021
DOIs	https://doi.org/10.1039/d0sc07047e
Publication status	Published - 21 Apr 2021

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@article{9195d45dddc14b49ab4f63c8b0e35a3b,

title = "Tandem [4 + 2]/[2 + 2] cycloaddition of o-carboryne with enynes: facile construction of carborane-fused tricyclics",

abstract = "o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. With 1-Li-2-OTf-o-C2B10H10 as the precursor, o-carboryne undergoes an efficient [4 + 2] cycloaddition with various conjugated enynes, followed by a subsequent [2 + 2] cycloaddition at room temperature, generating a series of carborane-fused tricyclo[6.4.0.02,7]dodeca-2,12-dienes in moderate to high isolated yields. This reaction is compatible with many functional groups and has a broad substrate scope. A reactive carborane-fused 1,2-cyclohexadiene intermediate is involved, which is supported by experimental results and DFT calculations. This protocol offers a convenient strategy for the construction of complex carborane-functionalized tricyclics.",

author = "Jie Zhang and Zuowei Xie",

note = "Publisher Copyright: {\textcopyright} 2021 The Author(s). Published by the Royal Society of Chemistry. Funding Information: This work was supported by grants from the Research Grants Council of HKSAR (Project No. 14306519) and NSFC/RGC Joint Research Scheme (Project No. N\_CUHK402/18), as well as by the CUHK Impact Postdoctoral Fellowship Scheme (IPDFS to Z.J.).",

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doi = "10.1039/d0sc07047e",

language = "English",

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T1 - Tandem [4 + 2]/[2 + 2] cycloaddition of o-carboryne with enynes

T2 - facile construction of carborane-fused tricyclics

AU - Zhang, Jie

AU - Xie, Zuowei

N1 - Publisher Copyright: © 2021 The Author(s). Published by the Royal Society of Chemistry. Funding Information: This work was supported by grants from the Research Grants Council of HKSAR (Project No. 14306519) and NSFC/RGC Joint Research Scheme (Project No. N_CUHK402/18), as well as by the CUHK Impact Postdoctoral Fellowship Scheme (IPDFS to Z.J.).

PY - 2021/4/21

Y1 - 2021/4/21

N2 - o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. With 1-Li-2-OTf-o-C2B10H10 as the precursor, o-carboryne undergoes an efficient [4 + 2] cycloaddition with various conjugated enynes, followed by a subsequent [2 + 2] cycloaddition at room temperature, generating a series of carborane-fused tricyclo[6.4.0.02,7]dodeca-2,12-dienes in moderate to high isolated yields. This reaction is compatible with many functional groups and has a broad substrate scope. A reactive carborane-fused 1,2-cyclohexadiene intermediate is involved, which is supported by experimental results and DFT calculations. This protocol offers a convenient strategy for the construction of complex carborane-functionalized tricyclics.

AB - o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. With 1-Li-2-OTf-o-C2B10H10 as the precursor, o-carboryne undergoes an efficient [4 + 2] cycloaddition with various conjugated enynes, followed by a subsequent [2 + 2] cycloaddition at room temperature, generating a series of carborane-fused tricyclo[6.4.0.02,7]dodeca-2,12-dienes in moderate to high isolated yields. This reaction is compatible with many functional groups and has a broad substrate scope. A reactive carborane-fused 1,2-cyclohexadiene intermediate is involved, which is supported by experimental results and DFT calculations. This protocol offers a convenient strategy for the construction of complex carborane-functionalized tricyclics.

UR - https://www.scopus.com/pages/publications/85104832159

U2 - 10.1039/d0sc07047e

DO - 10.1039/d0sc07047e

M3 - Journal article

AN - SCOPUS:85104832159

SN - 2041-6520

VL - 12

SP - 5616

EP - 5620

JO - Chemical Science

JF - Chemical Science

IS - 15

ER -

Tandem [4 + 2]/[2 + 2] cycloaddition of o-carboryne with enynes: facile construction of carborane-fused tricyclics

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