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 journalArticle

23 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 languageEnglish
Pages (from-to)5810-5813
Number of pages4
JournalOrganic Letters
Volume15
Issue number22
DOIs
Publication statusPublished - Nov 15 2013
Externally publishedYes

Fingerprint

cyanogen
Alkynes
Iodides
alkynes
iodides
Copper
copper
Cyanides
cyanides
Experiments

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Okamoto, K., Watanabe, M., Sakata, N., Murai, M., & Ohe, K. (2013). Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide. Organic Letters, 15(22), 5810-5813. https://doi.org/10.1021/ol402863g

Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide. / Okamoto, Kazuhiro; Watanabe, Masahito; Sakata, Naoki; Murai, Masahito; Ohe, Kouichi.

In: Organic Letters, Vol. 15, No. 22, 15.11.2013, p. 5810-5813.

Research output: Contribution to journalArticle

Okamoto, K, Watanabe, M, Sakata, N, Murai, M & Ohe, K 2013, 'Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide', Organic Letters, vol. 15, no. 22, pp. 5810-5813. https://doi.org/10.1021/ol402863g
Okamoto K, Watanabe M, Sakata N, Murai M, Ohe K. Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide. Organic Letters. 2013 Nov 15;15(22):5810-5813. https://doi.org/10.1021/ol402863g
Okamoto, Kazuhiro ; Watanabe, Masahito ; Sakata, Naoki ; Murai, Masahito ; Ohe, Kouichi. / Copper-catalyzed C-H cyanation of terminal alkynes with cyanogen iodide. In: Organic Letters. 2013 ; Vol. 15, No. 22. pp. 5810-5813.
@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 = "11",
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

VL - 15

SP - 5810

EP - 5813

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -