Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C2B10H10 as Precursor

Jie Zhang; Zaozao Qiu; Zuowei Xie

doi:10.1021/acs.organomet.7b00574

Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C₂B₁₀H₁₀ as Precursor

Jie Zhang
, Zaozao Qiu^*
, Zuowei Xie

^*Corresponding author for this work

Department of Chemistry

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

13 Citations (Scopus)

Abstract

o-Carboryne (1,2-dehydro-o-carborane) generated in situ from 1-Li-2-OTf-o-C₂B₁₀H₁₀ undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant [4 + 2] cycloaddition products have been carried out, affording various multifunctionalized o-carboranes.

Original language	English
Pages (from-to)	3806-3811
Number of pages	6
Journal	Organometallics
Volume	36
Issue number	19
Early online date	26 Sept 2017
DOIs	https://doi.org/10.1021/acs.organomet.7b00574
Publication status	Published - 9 Oct 2017

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@article{e82629cdf27d4bcc928680963c83c563,

title = "Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C2B10H10 as Precursor",

abstract = "o-Carboryne (1,2-dehydro-o-carborane) generated in situ from 1-Li-2-OTf-o-C2B10H10 undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant [4 + 2] cycloaddition products have been carried out, affording various multifunctionalized o-carboranes.",

author = "Jie Zhang and Zaozao Qiu and Zuowei Xie",

note = "This work was supported by grants from RGC of the Hong Kong Special Administration Region (project no. 14306114 to Z.X.), the National Natural Sciences Foundation of China (project no. 21372245 to Z.Q.), NSFC-RGC Joint Research Scheme (project no. N\_CUHK442/14 to Z.X.), and CAS-Croucher Funding Scheme. We thank Ms. Hoi-Shan Chan for single-crystal X-ray analyses. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = oct,

day = "9",

doi = "10.1021/acs.organomet.7b00574",

language = "English",

volume = "36",

pages = "3806--3811",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C2B10H10 as Precursor

AU - Zhang, Jie

AU - Qiu, Zaozao

AU - Xie, Zuowei

N1 - This work was supported by grants from RGC of the Hong Kong Special Administration Region (project no. 14306114 to Z.X.), the National Natural Sciences Foundation of China (project no. 21372245 to Z.Q.), NSFC-RGC Joint Research Scheme (project no. N_CUHK442/14 to Z.X.), and CAS-Croucher Funding Scheme. We thank Ms. Hoi-Shan Chan for single-crystal X-ray analyses. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/10/9

Y1 - 2017/10/9

N2 - o-Carboryne (1,2-dehydro-o-carborane) generated in situ from 1-Li-2-OTf-o-C2B10H10 undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant [4 + 2] cycloaddition products have been carried out, affording various multifunctionalized o-carboranes.

AB - o-Carboryne (1,2-dehydro-o-carborane) generated in situ from 1-Li-2-OTf-o-C2B10H10 undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant [4 + 2] cycloaddition products have been carried out, affording various multifunctionalized o-carboranes.

UR - https://www.scopus.com/pages/publications/85030861583

U2 - 10.1021/acs.organomet.7b00574

DO - 10.1021/acs.organomet.7b00574

M3 - Journal article

AN - SCOPUS:85030861583

SN - 0276-7333

VL - 36

SP - 3806

EP - 3811

JO - Organometallics

JF - Organometallics

IS - 19

ER -

Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C₂B₁₀H₁₀ as Precursor

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