Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide

Kazuhiro Okamoto; Masahito Watanabe; Naoki Sakata; Masahito Murai; Kouichi Ohe

doi:10.1021/ol402863g

Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide

Kazuhiro Okamoto, Masahito Watanabe, Naoki Sakata, Masahito Murai, Kouichi Ohe

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

35 Citations (Scopus)

Abstract

A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) that produces alkynyl cyanides has been developed. The use of tetramethylpiperidine as a sterically congested base was successful in this reaction. Some control experiments revealed that the reaction involves the noncatalyzed formation of alkynyl iodides followed by copper-catalyzed cyanation of the iodides without the formation of copper(I) acetylide. This observation contrasts with what is normally observed in various copper-mediated reactions using terminal alkynes.

Original language	English
Pages (from-to)	5810-5813
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	22
DOIs	https://doi.org/10.1021/ol402863g
Publication status	Published - Nov 15 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol402863g

Cite this

@article{c2ca67f98e82419d8020d92cd0ae78a2,

title = "Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide",

abstract = "A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) that produces alkynyl cyanides has been developed. The use of tetramethylpiperidine as a sterically congested base was successful in this reaction. Some control experiments revealed that the reaction involves the noncatalyzed formation of alkynyl iodides followed by copper-catalyzed cyanation of the iodides without the formation of copper(I) acetylide. This observation contrasts with what is normally observed in various copper-mediated reactions using terminal alkynes.",

author = "Kazuhiro Okamoto and Masahito Watanabe and Naoki Sakata and Masahito Murai and Kouichi Ohe",

year = "2013",

month = nov,

day = "15",

doi = "10.1021/ol402863g",

language = "English",

volume = "15",

pages = "5810--5813",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide

AU - Okamoto, Kazuhiro

AU - Watanabe, Masahito

AU - Sakata, Naoki

AU - Murai, Masahito

AU - Ohe, Kouichi

PY - 2013/11/15

Y1 - 2013/11/15

N2 - A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) that produces alkynyl cyanides has been developed. The use of tetramethylpiperidine as a sterically congested base was successful in this reaction. Some control experiments revealed that the reaction involves the noncatalyzed formation of alkynyl iodides followed by copper-catalyzed cyanation of the iodides without the formation of copper(I) acetylide. This observation contrasts with what is normally observed in various copper-mediated reactions using terminal alkynes.

AB - A copper-catalyzed reaction of terminal alkynes with cyanogen iodide (ICN) that produces alkynyl cyanides has been developed. The use of tetramethylpiperidine as a sterically congested base was successful in this reaction. Some control experiments revealed that the reaction involves the noncatalyzed formation of alkynyl iodides followed by copper-catalyzed cyanation of the iodides without the formation of copper(I) acetylide. This observation contrasts with what is normally observed in various copper-mediated reactions using terminal alkynes.

UR - http://www.scopus.com/inward/record.url?scp=84887974518&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84887974518&partnerID=8YFLogxK

U2 - 10.1021/ol402863g

DO - 10.1021/ol402863g

M3 - Article

AN - SCOPUS:84887974518

SN - 1523-7060

VL - 15

SP - 5810

EP - 5813

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this