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. 2018 Jul 11;140(27):8434-8438.
doi: 10.1021/jacs.8b05421. Epub 2018 Jun 26.

Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes

Vu T Nguyen  1 , Hang T Dang  1 , Hoang H Pham  1 , Viet D Nguyen  1 , Carsten Flores-Hansen  1 , Hadi D Arman  1 , Oleg V Larionov  1
Affiliations

Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes

Vu T Nguyen et al. J Am Chem Soc. .

Abstract

Conjugated dienes and polyenes are typically synthesized by sequential introduction of C═C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C═C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging dienes containing cis double bonds. We also show that the reaction can serve as a synthetic platform for the construction of conjugated polyenes.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Scheme 1.
Scheme 1.
Synthesis of conjugated dienes and polyenes
See this image and copyright information in PMC

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