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^*

^*Corresponding author for this work

Department of Chemistry

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

17 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
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c6cc08601b

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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 = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6cc08601b",

language = "English",

volume = "52",

pages = "14404--14407",

journal = "Chemical Communications",

issn = "1359-7345",

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 - Publisher Copyright: © The Royal Society of Chemistry.

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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UR - http://www.scopus.com/inward/citedby.url?scp=85006279479&partnerID=8YFLogxK

U2 - 10.1039/c6cc08601b

DO - 10.1039/c6cc08601b

M3 - Article

AN - SCOPUS:85006279479

SN - 1359-7345

VL - 52

SP - 14404

EP - 14407

JO - Chemical Communications

JF - Chemical Communications

IS - 100

ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1511557: Experimental Crystal Structure Determination

CCDC 1511556: Experimental Crystal Structure Determination

CCDC 1511558: Experimental Crystal Structure Determination

Cite this

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1511557: Experimental Crystal Structure Determination

CCDC 1511556: Experimental Crystal Structure Determination

CCDC 1511558: Experimental Crystal Structure Determination

Cite this