Pd-Catalyzed Selective Bifunctionalization of 3-Iodo-o-Carborane by Pd Migration

Yixiu Ge; Jie Zhang; Zaozao Qiu; Zuowei Xie

doi:10.1002/anie.201914500

Pd-Catalyzed Selective Bifunctionalization of 3-Iodo-o-Carborane by Pd Migration

Yixiu Ge
, Jie Zhang
, Zaozao Qiu^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

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

61 Citations (Scopus)

Abstract

A palladium-catalyzed highly selective 3,4-bifunctionalization of 3-I-o-carborane has been developed, leading to the preparation of 3-alkenyl-4-R-o-carboranes (R=alkyl, alkynyl, aryl, allyl, CN, and amido) in high to excellent yields. This protocol combines the sequential activation of cage B(3)−I and B(4)−H bonds by Pd migration from exo-alkenyl sp² C to cage B(4), which is driven by thermodynamic force. This represents a brand-new strategy for selective bifunctionalization of carboranes with two different substituents.

Original language	English
Pages (from-to)	4851-4855
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	12
Early online date	9 Mar 2020
DOIs	https://doi.org/10.1002/anie.201914500
Publication status	Published - 16 Mar 2020

User-Defined Keywords

B−H activation
carborane
catalysis
migration
palladium

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

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10.1002/anie.201914500

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@article{54207b79aa5f40039b3f437cbb01bb70,

title = "Pd-Catalyzed Selective Bifunctionalization of 3-Iodo-o-Carborane by Pd Migration",

abstract = "A palladium-catalyzed highly selective 3,4-bifunctionalization of 3-I-o-carborane has been developed, leading to the preparation of 3-alkenyl-4-R-o-carboranes (R=alkyl, alkynyl, aryl, allyl, CN, and amido) in high to excellent yields. This protocol combines the sequential activation of cage B(3)−I and B(4)−H bonds by Pd migration from exo-alkenyl sp2 C to cage B(4), which is driven by thermodynamic force. This represents a brand-new strategy for selective bifunctionalization of carboranes with two different substituents.",

keywords = "B−H activation, carborane, catalysis, migration, palladium",

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

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim. Funding Information: This work was supported by grants from National Natural Science Foundation of China (No. 21772223 to Z.Q.), the Science and Technology Commission of Shanghai Municipality (No. 18590760800), the Chinese Academy of Sciences, and Hong Kong RGC (No. 14305018 and 14305918).",

year = "2020",

month = mar,

day = "16",

doi = "10.1002/anie.201914500",

language = "English",

volume = "59",

pages = "4851--4855",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons Ltd",

number = "12",

}

TY - JOUR

T1 - Pd-Catalyzed Selective Bifunctionalization of 3-Iodo-o-Carborane by Pd Migration

AU - Ge, Yixiu

AU - Zhang, Jie

AU - Qiu, Zaozao

AU - Xie, Zuowei

N1 - Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Funding Information: This work was supported by grants from National Natural Science Foundation of China (No. 21772223 to Z.Q.), the Science and Technology Commission of Shanghai Municipality (No. 18590760800), the Chinese Academy of Sciences, and Hong Kong RGC (No. 14305018 and 14305918).

PY - 2020/3/16

Y1 - 2020/3/16

N2 - A palladium-catalyzed highly selective 3,4-bifunctionalization of 3-I-o-carborane has been developed, leading to the preparation of 3-alkenyl-4-R-o-carboranes (R=alkyl, alkynyl, aryl, allyl, CN, and amido) in high to excellent yields. This protocol combines the sequential activation of cage B(3)−I and B(4)−H bonds by Pd migration from exo-alkenyl sp2 C to cage B(4), which is driven by thermodynamic force. This represents a brand-new strategy for selective bifunctionalization of carboranes with two different substituents.

AB - A palladium-catalyzed highly selective 3,4-bifunctionalization of 3-I-o-carborane has been developed, leading to the preparation of 3-alkenyl-4-R-o-carboranes (R=alkyl, alkynyl, aryl, allyl, CN, and amido) in high to excellent yields. This protocol combines the sequential activation of cage B(3)−I and B(4)−H bonds by Pd migration from exo-alkenyl sp2 C to cage B(4), which is driven by thermodynamic force. This represents a brand-new strategy for selective bifunctionalization of carboranes with two different substituents.

KW - B−H activation

KW - carborane

KW - catalysis

KW - migration

KW - palladium

UR - https://www.scopus.com/pages/publications/85078879265

U2 - 10.1002/anie.201914500

DO - 10.1002/anie.201914500

M3 - Journal article

C2 - 31875431

AN - SCOPUS:85078879265

SN - 1433-7851

VL - 59

SP - 4851

EP - 4855

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Pd-Catalyzed Selective Bifunctionalization of 3-Iodo-o-Carborane by Pd Migration

Abstract

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