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. 2014 Apr 14;356(6):1359-1369.
doi: 10.1002/adsc.201300904.

Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes

Yi-Yun Yu  1 , Gunda I Georg  1
Affiliations

Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes

Yi-Yun Yu et al. Adv Synth Catal. .

Abstract

A green and mild protocol for the dehydrogenative olefination of cyclic enaminones was devised via palladium catalysis at room temperature using oxygen as the terminal oxidant. The synthetic utility of the olefinated cyclic enaminones afforded a series of unique 1,3,5-trisubstituted benzenes via an unanticipated Diels-Alder tandem reaction. The broad substrate scope and good yields achieved with this new protocol provide an alternative pathway for arene functionalization.

Keywords: C–H activation; arenes; cycloaddition; olefination; palladium.

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Figures

Scheme 1
Scheme 1
C–H alkenylation of cyclic enaminones.
Scheme 2
Scheme 2
Biomimetic aerobic Pd catalysis with catechol.
Scheme 3
Scheme 3
Formation of 1,3,5-trisubstituted benzenes.
Scheme 4
Scheme 4
Tandem reactions featuring (a) decarboxylation and (b) retro-Mannich fragmentation.
Scheme 5
Scheme 5
One-pot synthesis of trisubstituted benzene 43.
See this image and copyright information in PMC

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