Palladium-catalyzed coupling of 3-indolyl triflate. Syntheses of 3-vinyl and 3-alkynylindoles

Article abstract of DOI:10.1080/00397919208019065

Palladium-catalyzed coupling of 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkynes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).

Full text of DOI:10.1080/00397919208019065

This article was downloaded by: [University of Glasgow]
On: 10 September 2013, At: 07:38
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Palladium-Catalyzed Coupling
of 3-Indolyl Triflate. Syntheses
of 3-Vinyl and 3-Alkynylindoles
Gordon W. Gribble a & Samuel C. Conway a
a Department of Chemistry, Dartmouth College,
Hanover, New Hampshire, 03755
Published online: 24 Sep 2006.
To cite this article: Gordon W. Gribble & Samuel C. Conway (1992) Palladium-
Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles,
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 22:15, 2129-2141
To link to this article: http://dx.doi.org/10.1080/00397919208019065
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,

and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions