Pd(ii)-catalyzed synthesis of bifunctionalized carboranes via cage B-H activation of 1-CH2 NH2 -o -carboranes

Chemical Science
Xiaolei Zhang, Hong Yan

Abstract

Aminoalkyl carboranes are anticipated to be valuable synthons toward the synthesis of bifunctionalized carboranes. However, direct cage boron derivation of these carborane derivatives has not been solved. Herein, the reversible conversion of catalytically infeasible o-carboranyl methylamines (1-CH2NH2-o-carboranes) into bidentate imines initiates Pd-mediated cage B-H activation. As a result, an amine coordinated bicyclic Pd(ii) complex (3) has been isolated and proven to be the catalytically active intermediate for highly site-selective B-H diarylation of o-carboranyl methylamines. Using glyoxylic acid as an inexpensive and commercially available transient directing reagent, a wide range of cage B(4,5)-diarylated free primary o-carboranyl methylamines were prepared in good to excellent yields with the avoidance of the pre-installation and removal of a directing group. This method provides easy access to cage boron functionalized o-carboranyl methylamines with potential for application in pharmaceuticals.

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Citations

Apr 27, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yangjian QuanZuowei Xie
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
May 26, 2018·Organic & Biomolecular Chemistry·Sahra St John-Campbell, James A Bull
May 16, 2019·Chemical Society Reviews·Yangjian Quan, Zuowei Xie
Dec 29, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Run-Ze YuanGuo-Xin Jin
Jan 19, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Yixiu GeZuowei Xie
Dec 30, 2020·Angewandte Chemie·Meng ChenHong Yan
Jul 24, 2021·Chemical Communications : Chem Comm·Yixiu GeZuowei Xie
Jul 22, 2021·Chemistry : a European Journal·Clément JacobGwilherm Evano
Feb 26, 2019·Journal of the American Chemical Society·Hairong LyuZuowei Xie
Sep 21, 2018·Journal of the American Chemical Society·Furong LinSimon Duttwyler
Jul 16, 2019·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Dec 30, 2021·Inorganic Chemistry·Yatong FuJu-You Lu

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Methods Mentioned

BETA
neutron capture therapy
X-ray
NMR
infrared spectroscopy

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