First evidence of 1,3-bis-indolylallenes: Generation by a sequential double nucleophilic process from ynones

Iaroslav Baglai (1, 2, 3) , Valérie Maraval (1) , Zoia Voitenko (3) , Carine Guyard-Duhayon (1) , Yulian M. Volovenko (3) , Rémi Chauvin (1)

1 LCC - Laboratoire de chimie de coordination
2 ICT - Institut de Chimie de Toulouse
3 National Taras Shevchenko University of Kiev

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. 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.

Domaines: Chimie de coordination

Iaroslav Baglai, Valérie Maraval, Zoia Voitenko, Carine Guyard-Duhayon, Yulian M. Volovenko, et al.. First evidence of 1,3-bis-indolylallenes: Generation by a sequential double nucleophilic process from ynones. Synthetic Communications, 2015, 45 (2), pp.253-261. ⟨10.1080/00397911.2014.961198⟩. ⟨hal-01916645⟩