Ruthenium-catalyzed regioselective 1,3-methylene transfer by cleavage of two adjacent sigma-carbon-carbon bonds: an easy and selective synthesis of highly substituted benzenes

Ruthenium-catalyzed regioselective 1,3-methylene transfer by cleavage of two adjacent sigma-carbon-carbon bonds: an easy and selective synthesis of highly substituted benzenes

We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring,...

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Veröffentlicht in:Journal of the American Chemical Society 2005-03, Vol.127 (12), p.4186-4187
Hauptverfasser: Lian, Jian-Jou, Odedra, Arjan, Wu, Chang-Jung, Liu, Rai-Shung
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container_title Journal of the American Chemical Society
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creator Lian, Jian-Jou
Odedra, Arjan
Wu, Chang-Jung
Liu, Rai-Shung
description We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.
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title Ruthenium-catalyzed regioselective 1,3-methylene transfer by cleavage of two adjacent sigma-carbon-carbon bonds: an easy and selective synthesis of highly substituted benzenes
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