CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates

Zhen Yuan Liao; Pen Yuan Liao; Tun Cheng Chien

doi:10.1039/c6cc08601b

CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates

Zhen Yuan Liao, Pen Yuan Liao, Tun Cheng Chien

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.

Original language	English
Pages (from-to)	14404-14407
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	100
DOIs	https://doi.org/10.1039/c6cc08601b
Publication status	Published - 2016

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates",

abstract = "CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.",

author = "Liao, {Zhen Yuan} and Liao, {Pen Yuan} and Chien, {Tun Cheng}",

note = "Funding Information: This work was supported by Research Grants 104-2113-M-003-001 and 105-2113-M-003-003 from the Ministry of Science and Technology, Taiwan. We also thank Professor Ming-Chang P. Yeh (National Taiwan Normal University, NTNU) for his helpful discussion and Mr Ting-Shen Kuo (NTNU) for his assistance with X-ray crystallographic analysis.",

year = "2016",

doi = "10.1039/c6cc08601b",

language = "English",

volume = "52",

pages = "14404--14407",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

number = "100",

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TY - JOUR

T1 - CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates

AU - Liao, Zhen Yuan

AU - Liao, Pen Yuan

AU - Chien, Tun Cheng

N1 - Funding Information: This work was supported by Research Grants 104-2113-M-003-001 and 105-2113-M-003-003 from the Ministry of Science and Technology, Taiwan. We also thank Professor Ming-Chang P. Yeh (National Taiwan Normal University, NTNU) for his helpful discussion and Mr Ting-Shen Kuo (NTNU) for his assistance with X-ray crystallographic analysis.

PY - 2016

Y1 - 2016

N2 - CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.

AB - CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.

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CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates

Abstract

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