A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

Michael O. Frederick; Jason A. Mulder; Michael R. Tracey; Richard P. Hsung; Jian Huang; Kimberly C.M. Kurtz; Lichun Shen; Christopher J. Douglas

doi:10.1021/ja021304j

A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

Michael O. Frederick
, Jason A. Mulder
, Michael R. Tracey
, Richard P. Hsung
, Jian Huang
, Kimberly C.M. Kurtz
, Lichun Shen
, Christopher J. Douglas

Chemistry (Twin Cities)

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

237 Scopus citations

Abstract

A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.

Original language	English (US)
Pages (from-to)	2368-2369
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	9
DOIs	https://doi.org/10.1021/ja021304j
State	Published - Mar 5 2003

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10.1021/ja021304j

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title = "A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides",

abstract = "A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.",

author = "Frederick, \{Michael O.\} and Mulder, \{Jason A.\} and Tracey, \{Michael R.\} and Hsung, \{Richard P.\} and Jian Huang and Kurtz, \{Kimberly C.M.\} and Lichun Shen and Douglas, \{Christopher J.\}",

year = "2003",

month = mar,

day = "5",

doi = "10.1021/ja021304j",

language = "English (US)",

volume = "125",

pages = "2368--2369",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

AU - Frederick, Michael O.

AU - Mulder, Jason A.

AU - Tracey, Michael R.

AU - Hsung, Richard P.

AU - Huang, Jian

AU - Kurtz, Kimberly C.M.

AU - Shen, Lichun

AU - Douglas, Christopher J.

PY - 2003/3/5

Y1 - 2003/3/5

N2 - A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.

AB - A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.

UR - https://www.scopus.com/pages/publications/0037420370

UR - https://www.scopus.com/pages/publications/0037420370#tab=citedBy

U2 - 10.1021/ja021304j

DO - 10.1021/ja021304j

M3 - Article

C2 - 12603105

AN - SCOPUS:0037420370

SN - 0002-7863

VL - 125

SP - 2368

EP - 2369

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

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