Catalytic Regioselective Cage B(8)-H Arylation of o-Carboranes via "Cage-Walking" Strategy

Journal of the American Chemical Society
Hairong LyuZuowei Xie

Abstract

A proof-of-concept example of catalytic regioselective cage B(8)-H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced "cage-walking" from B(4) to B(8) vertex is proposed to account for the regioselective B(8)-H activation.

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Citations

Apr 27, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yangjian QuanZuowei Xie
May 16, 2019·Chemical Communications : Chem Comm·Ying-Ying Xue, Yi-Hong Ding
Jun 25, 2019·Angewandte Chemie·Zhongming YangHong Yan
Jan 16, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Chun-Xiao CuiZuowei Xie
Feb 6, 2020·Chemistry : a European Journal·Guang-Ao YuChang-Duo Yue
Jan 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ke CaoJunxiao Yang
May 16, 2019·Chemical Society Reviews·Yangjian Quan, Zuowei Xie
Jan 19, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Yixiu GeZuowei Xie
Dec 30, 2020·Angewandte Chemie·Meng ChenHong Yan
Mar 16, 2021·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Apr 3, 2020·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Jul 14, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Hui LiZifan Ma
Jul 24, 2021·Chemical Communications : Chem Comm·Yixiu GeZuowei Xie
Jul 16, 2019·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Aug 16, 2019·Organic Process Research & Development·Rafal M DziedzicAlexander M Spokoyny
Dec 3, 2021·Inorganic Chemistry·Harrison A MillsAlexander M Spokoyny

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