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. 2019 Jun 10;9(32):18191-18195.
doi: 10.1039/c9ra04142g.

Rh(iii)-catalyzed C-7 arylation of indolines with arylsilanes via C-H activation

Haiqing Luo  1 , Qi Xie  1 , Kai Sun  1 , Jianbo Deng  1 , Lin Xu  1 , Kejun Wang  1 , Xuzhong Luo  1
Affiliations

Rh(iii)-catalyzed C-7 arylation of indolines with arylsilanes via C-H activation

Haiqing Luo et al. RSC Adv. .

Abstract

Site-selective synthesis of C-7 arylated indolines has been achieved via oxidative arylation of indolines with arylsilanes under Rh(iii)-catalyzed C-H activation of indolines by using CuSO4 as a co-oxidant. This transformation has been explored for a wide range of substrates under mild conditions.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. C-2 arylation of indoles with arylsilanes and C-7 arylation of indolines.
Scheme 2
Scheme 2. Rh(iii)-catalyzed the direct C-8 arylation of N-(2-pyrimidyl)-tetrahydroquinoline 5 with phenyltriethoxysilane 2a.
Scheme 3
Scheme 3. Transformation of C-7-arylated indoline 3fa to the corresponding indole 7a.
Scheme 4
Scheme 4. Parallel kinetic isotope experiment.
Scheme 5
Scheme 5. Plausible catalytic cycle for Rh(iii)-catalyzed the direct C-7 arylation of indolines with phenyltriethoxysilane.
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