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Pd‐Catalyzed Selective Bifunctionalization of 3‐Iodo‐ o ‐Carborane by Pd Migration
Author(s) -
Ge Yixiu,
Zhang Jie,
Qiu Zaozao,
Xie Zuowei
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914500
Subject(s) - carborane , chemistry , catalysis , alkyl , aryl , palladium , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
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 sp 2 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.