Diboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond

Minling Zhong; Jie Zhang; Zhenpin Lu; Zuowei Xie

doi:10.1039/d1dt03665c

Diboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond

Minling Zhong
, Jie Zhang
, Zhenpin Lu^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

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

10 Citations (Scopus)

Abstract

Small ring compounds are fascinating molecules and have been used as valuable compounds in organic synthesis. In this study, a carborane-fused four-membered boracycle bearing an electron precise B–B bond, 1,2-[BBrSMe₂]₂-o-C₂B₁₀H₁₀, was synthesized via the reaction of 1,2-Li₂-o-carborane with B₂Br₄(SMe₂)₂. This novel boracycle can be used as a “strain-release” compound to achieve diboration of alkenes and alkynes, leading to the generation of ring-expansion products. Interestingly, when bis(trimethylsilyl) acetylene was employed, an allene-functionalized six-membered boracycle was obtained. Moreover, DFT calculations were conducted to shed light on the reaction mechanism.

Original language	English
Pages (from-to)	17150-17155
Number of pages	6
Journal	Dalton Transactions
Volume	50
Issue number	46
Early online date	10 Nov 2021
DOIs	https://doi.org/10.1039/d1dt03665c
Publication status	Published - 14 Dec 2021

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10.1039/d1dt03665c

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title = "Diboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond",

abstract = "Small ring compounds are fascinating molecules and have been used as valuable compounds in organic synthesis. In this study, a carborane-fused four-membered boracycle bearing an electron precise B–B bond, 1,2-[BBrSMe2]2-o-C2B10H10, was synthesized via the reaction of 1,2-Li2-o-carborane with B2Br4(SMe2)2. This novel boracycle can be used as a “strain-release” compound to achieve diboration of alkenes and alkynes, leading to the generation of ring-expansion products. Interestingly, when bis(trimethylsilyl) acetylene was employed, an allene-functionalized six-membered boracycle was obtained. Moreover, DFT calculations were conducted to shed light on the reaction mechanism. ",

author = "Minling Zhong and Jie Zhang and Zhenpin Lu and Zuowei Xie",

note = "Funding information: This work was supported by a grant from the Research Grants Council of The Hong Kong Special Administration Region (Project No. 14303621). J. Z. thanks CUHK Impact Postdoctoral Fellowship Scheme (IPDFS) for support. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021",

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T1 - Diboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond

AU - Zhong, Minling

AU - Zhang, Jie

AU - Lu, Zhenpin

AU - Xie, Zuowei

N1 - Funding information: This work was supported by a grant from the Research Grants Council of The Hong Kong Special Administration Region (Project No. 14303621). J. Z. thanks CUHK Impact Postdoctoral Fellowship Scheme (IPDFS) for support. Publisher Copyright: © The Royal Society of Chemistry 2021

PY - 2021/12/14

Y1 - 2021/12/14

N2 - Small ring compounds are fascinating molecules and have been used as valuable compounds in organic synthesis. In this study, a carborane-fused four-membered boracycle bearing an electron precise B–B bond, 1,2-[BBrSMe2]2-o-C2B10H10, was synthesized via the reaction of 1,2-Li2-o-carborane with B2Br4(SMe2)2. This novel boracycle can be used as a “strain-release” compound to achieve diboration of alkenes and alkynes, leading to the generation of ring-expansion products. Interestingly, when bis(trimethylsilyl) acetylene was employed, an allene-functionalized six-membered boracycle was obtained. Moreover, DFT calculations were conducted to shed light on the reaction mechanism.

AB - Small ring compounds are fascinating molecules and have been used as valuable compounds in organic synthesis. In this study, a carborane-fused four-membered boracycle bearing an electron precise B–B bond, 1,2-[BBrSMe2]2-o-C2B10H10, was synthesized via the reaction of 1,2-Li2-o-carborane with B2Br4(SMe2)2. This novel boracycle can be used as a “strain-release” compound to achieve diboration of alkenes and alkynes, leading to the generation of ring-expansion products. Interestingly, when bis(trimethylsilyl) acetylene was employed, an allene-functionalized six-membered boracycle was obtained. Moreover, DFT calculations were conducted to shed light on the reaction mechanism.

UR - https://www.scopus.com/pages/publications/85120695059

U2 - 10.1039/d1dt03665c

DO - 10.1039/d1dt03665c

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C2 - 34780587

AN - SCOPUS:85120695059

SN - 1477-9226

VL - 50

SP - 17150

EP - 17155

JO - Dalton Transactions

JF - Dalton Transactions

IS - 46

ER -

Diboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond

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