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5. Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)–H Bonds Enabled by Cobalt Catalysis

Author

Yu-He Kan, Changdong Shao, Xin Ding, Huayou Hu, Hu Zhengsong, Haiqing Luo, Ming-Zhu Lu, Sanjun Zhi, and Teck-Peng Loh

Subjects
Indole test, Steric effects, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Biochemistry, Copper, Combinatorial chemistry, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Molecule, Physical and Theoretical Chemistry, Bifunctional, Cobalt
Abstract

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

Published
2020

6. Directed Palladium(II)-Catalyzed Intermolecular Anti-Markovnikov Hydroarylation of Unactivated Alkenes with (Hetero)arylsilanes

Author

Haiqing Luo, Hu Zhengsong, Changdong Shao, Ming-Zhu Lu, Yu-He Kan, and Teck-Peng Loh

Subjects
Steric effects, Denticity, 010405 organic chemistry, Organic Chemistry, Markovnikov's rule, chemistry.chemical_element, Regioselectivity, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Functional group, Physical and Theoretical Chemistry, Selectivity, Palladium
Abstract

We describe herein a regioselective palladium(II)-catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-aminoquinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.

Published
2020

10. Generation and Trapping of a 1-Phosphafulvene: An Illustration of the PC/CC Analogy

Author

Hu, Zhengsong, Tian, Rongqiang, Zhao, Kang, Liu, Yanjie, Duan, Zheng, and Mathey, François

Abstract

1-Phosphafulvenes can be easily generated by dissociation of dimers resulting from the reaction of phospholes with aldimines. As electron-rich partners, they act as 4π phosphadienic systems toward alkenes and alkynes in [4 + 2] cycloaddition reactions. As electron-poor partners, they act either as 2π systems toward conjugated dienes in [2 + 4] cycloaddition reactions via their PC double bond or as 6π systems toward phosphadienes in [6 + 4] cycloaddition reactions.

Published
2024
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18. Reaction of Phospholes with Aldimines: A One-StepSynthesis of Chelating, Alpha-C2-BridgedBiphospholes.

Author

Hu, Zhengsong, Li, Zongyang, Zhao, Kang, Tian, Rongqiang, Duan, Zheng, and Mathey, François

Subjects
*PHOSPHOLES, *ALDIMINES, *CHELATING agents, *DIMERIZATION, *LEWIS acids
Abstract

Phospholesreact with aldimines at 170 °C in the presence of mild Lewisacids to give C2-bridged biphospholes in good yields. Themechanism includes a series of [1,5] shifts of the P-substituentsaround the phosphole ring, a P–H + aldimine condensation, andthe formation of a transient three-membered ring that dimerizes. [ABSTRACT FROM AUTHOR]

Published
2015
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20. Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp 2 )-H Bonds Enabled by Cobalt Catalysis.

Author

Lu MZ, Ding X, Shao C, Hu Z, Luo H, Zhi S, Hu H, Kan Y, and Loh TP

Abstract

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

Published
2020
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