Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

Miao Wang; Chau Ming So

doi:10.1021/acs.orglett.1c04138

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

Miao Wang, Chau Ming So

Research output: Journal article publication › Journal article › Academic research › peer-review

16 Citations (Scopus)

Abstract

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Original language	English
Pages (from-to)	681-685
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.1c04138
Publication status	Published - 3 Jan 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c04138

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title = "Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes",

abstract = "A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.",

author = "Miao Wang and So, {Chau Ming}",

note = "Funding Information: We thank the Research Grants Council of the Hong Kong Special Administrative Region, China (PolyU 15302821, 15300220, and 25301819), the National Natural Science Foundation of China (21972122), and the Shenzhen Municipal Science and Technology Innovation Commission (JCYJ20180306173843318) for financial support. We are grateful to Ms. Shan Shan Ng (PolyU) and Dr. On Ying Yuen (PolyU) for the preparation of supplementary material. Publisher Copyright: {\textcopyright} 2022 American Chemical Society",

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AU - So, Chau Ming

N1 - Funding Information: We thank the Research Grants Council of the Hong Kong Special Administrative Region, China (PolyU 15302821, 15300220, and 25301819), the National Natural Science Foundation of China (21972122), and the Shenzhen Municipal Science and Technology Innovation Commission (JCYJ20180306173843318) for financial support. We are grateful to Ms. Shan Shan Ng (PolyU) and Dr. On Ying Yuen (PolyU) for the preparation of supplementary material. Publisher Copyright: © 2022 American Chemical Society

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N2 - A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

AB - A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

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Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

Abstract

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