Diels-Alder Reaction of o-Carboryne with Fulvenes: Synthesis of Carboranonorbornadienes and Their Transformations

Jie Zhang; Zaozao Qiu; Peng-Fei Xu; Zuowei Xie

doi:10.1002/cplu.201402129

Diels-Alder Reaction of o-Carboryne with Fulvenes: Synthesis of Carboranonorbornadienes and Their Transformations

Jie Zhang
, Zaozao Qiu^*
, Peng-Fei Xu^*
, Zuowei Xie

^*Corresponding author for this work

Department of Chemistry

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

24 Citations (Scopus)

Abstract

o-Carboryne (1,2-dehydro-o-carborane) generated in situ from the precursor 1-iodo-2-lithio-o-carborane reacts with 6,6′-diarylfulvenes to give a series of carboranonorbornadienes in moderate yields with excellent regioselectivity. The resultant [4+2] cycloadducts can be further derivatized, thus leading to the formation of a variety of highly functionalized carboranes. This study shows that such Diels–Alder reaction serves as a convenient method for the preparation of a new class of multifunctionalized o-carborane derivatives that might find applications in medicine and materials science.

Original language	English
Pages (from-to)	1044-1052
Number of pages	9
Journal	ChemPlusChem
Volume	79
Issue number	7
DOIs	https://doi.org/10.1002/cplu.201402129
Publication status	Published - 1 Jul 2014

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

alkenes
carboranes
cycloaddition
hydrocarbons
synthetic methods

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10.1002/cplu.201402129

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title = "Diels-Alder Reaction of o-Carboryne with Fulvenes: Synthesis of Carboranonorbornadienes and Their Transformations",

abstract = "o-Carboryne (1,2-dehydro-o-carborane) generated in situ from the precursor 1-iodo-2-lithio-o-carborane reacts with 6,6′-diarylfulvenes to give a series of carboranonorbornadienes in moderate yields with excellent regioselectivity. The resultant [4+2] cycloadducts can be further derivatized, thus leading to the formation of a variety of highly functionalized carboranes. This study shows that such Diels–Alder reaction serves as a convenient method for the preparation of a new class of multifunctionalized o-carborane derivatives that might find applications in medicine and materials science.",

keywords = "alkenes, carboranes, cycloaddition, hydrocarbons, synthetic methods",

author = "Jie Zhang and Zaozao Qiu and Peng-Fei Xu and Zuowei Xie",

note = "National Natural Sciences Foundation of China. Grant Number: 21372245 Shanghai Pujiang Program. Grant Number: 13PJ1410800 Shanghai Science and Technology Committee. Grant Number: 13ZR1465000 The Research Grants Council of Hong Kong. Grant Number: 403912 Publisher Copyright : {\textcopyright} 2014 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2014",

month = jul,

day = "1",

doi = "10.1002/cplu.201402129",

language = "English",

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pages = "1044--1052",

journal = "ChemPlusChem",

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T1 - Diels-Alder Reaction of o-Carboryne with Fulvenes: Synthesis of Carboranonorbornadienes and Their Transformations

AU - Zhang, Jie

AU - Qiu, Zaozao

AU - Xu, Peng-Fei

AU - Xie, Zuowei

N1 - National Natural Sciences Foundation of China. Grant Number: 21372245 Shanghai Pujiang Program. Grant Number: 13PJ1410800 Shanghai Science and Technology Committee. Grant Number: 13ZR1465000 The Research Grants Council of Hong Kong. Grant Number: 403912 Publisher Copyright : © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2014/7/1

Y1 - 2014/7/1

N2 - o-Carboryne (1,2-dehydro-o-carborane) generated in situ from the precursor 1-iodo-2-lithio-o-carborane reacts with 6,6′-diarylfulvenes to give a series of carboranonorbornadienes in moderate yields with excellent regioselectivity. The resultant [4+2] cycloadducts can be further derivatized, thus leading to the formation of a variety of highly functionalized carboranes. This study shows that such Diels–Alder reaction serves as a convenient method for the preparation of a new class of multifunctionalized o-carborane derivatives that might find applications in medicine and materials science.

AB - o-Carboryne (1,2-dehydro-o-carborane) generated in situ from the precursor 1-iodo-2-lithio-o-carborane reacts with 6,6′-diarylfulvenes to give a series of carboranonorbornadienes in moderate yields with excellent regioselectivity. The resultant [4+2] cycloadducts can be further derivatized, thus leading to the formation of a variety of highly functionalized carboranes. This study shows that such Diels–Alder reaction serves as a convenient method for the preparation of a new class of multifunctionalized o-carborane derivatives that might find applications in medicine and materials science.

KW - alkenes

KW - carboranes

KW - cycloaddition

KW - hydrocarbons

KW - synthetic methods

U2 - 10.1002/cplu.201402129

DO - 10.1002/cplu.201402129

M3 - Journal article

SN - 2192-6506

VL - 79

SP - 1044

EP - 1052

JO - ChemPlusChem

JF - ChemPlusChem

IS - 7

ER -

Diels-Alder Reaction of o-Carboryne with Fulvenes: Synthesis of Carboranonorbornadienes and Their Transformations

Abstract

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