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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 2
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Original Articles

First Evidence of 1,3-Bis-indolylallenes: Generation by a Sequential Double Nucleophilic Process from Ynones

Iaroslav Baglai CNRS, LCC (Laboratoire de Chimie de Coordination), Toulouse, France; Université de Toulouse, Toulouse, France; Kiev National Taras Shevchenko University, Kiev, Ukraine
,
Valérie Maraval CNRS, LCC (Laboratoire de Chimie de Coordination), Toulouse, France; Université de Toulouse, Toulouse, FranceCorrespondence[email protected]
,
Zoia V. Voitenko Kiev National Taras Shevchenko University, Kiev, Ukraine
,
Carine Duhayon CNRS, LCC (Laboratoire de Chimie de Coordination), Toulouse, France; Université de Toulouse, Toulouse, France
,
Yulian M. Volovenko Kiev National Taras Shevchenko University, Kiev, Ukraine
&
Remi Chauvin CNRS, LCC (Laboratoire de Chimie de Coordination), Toulouse, France; Université de Toulouse, Toulouse, FranceCorrespondence[email protected]
Pages 253-261 | Received 22 Jul 2014, Published online: 26 Nov 2014
 
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Abstract

The first examples of 1,3-bis-indol-3-ylallenes (1,3-BIAs) are described. They have been generated by addition of a 3-lithioindole reactant to tetramethylsilane-protected mono- and di-alkynyl ketones. The one-pot preparation of 1,3-BIAs is enabled by both the double electrophilic character of the ynone substrates and the double nucleophilic character of the lithio-enamine function of the indolyl moiety, leading to a transient azafulvenium intermediate.

GRAPHICAL ABSTRACT

Notes

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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