facile-preparation-2z4e-dienamides-olefination-electron-deficient

Facile Preparation of (2<em>Z</em>,4<em>E</em>)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Direct cross-coupling between two alkenes via vinylic C-H bond activation represents an efficient strategy for the synthesis of butadienes with high ...

Hangzhou Normal University

A Ru-catalyzed direct olefination of electron-deficient alkenes with allyl acetate via C-H bond activation is disclosed. By using N,N-disubstituted aminocarbonyl as the directing group, this external oxidant-free protocol resulted in high reaction efficiency and good stereo- and regioselectivities, which opens a novel synthetic passway for access to (Z,E)-butadiene skeletons.

Olefination of Electron-Deficient Alkenes with Allyl Acetate: Stereo- and Regioselective Access to (2Z,4E)-Dienamides.

An oxidant-free cross-coupling reaction of electron-deficient alkenes using an inexpensive ruthenium catalyst is reported. With the assistance of the oxidizing directing group CONH(OMe), this protocol provides a mild, straightforward and efficient method for the preparation of valuable 1,3-butadiene skeletons with excellent Z,E selectivities.

A direct cross-coupling reaction of electron-deficient alkenes using an oxidizing directing group.

A rhodium-catalyzed Weinreb amide directed cross-coupling reaction between electron-deficient alkenes is reported, which provides an efficient route for the synthesis of valuable and versatile Weinreb amide functionalized (Z,E)-butadienes. The catalytic system is insensitive to water and oxygen and exhibits broad functional group tolerance. This method also allowed both terminal and internal alkenes as the cross-coupling partners.

Article	Year
Olefination of Electron-Deficient Alkenes with Allyl Acetate: Stereo- and Regioselective Access to (2Z,4E)-Dienamides. Organic letters\| PubMed ID: 27583399	2016
A direct cross-coupling reaction of electron-deficient alkenes using an oxidizing directing group. Chemical communications (Cambridge, England)\| PubMed ID: 27966727	2017
Weinreb amide directed cross-coupling reaction between electron-deficient alkenes catalyzed by a rhodium catalyst. Organic & biomolecular chemistry\| PubMed ID: 28098326	2017

Chunbing Yu

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