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Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates.

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A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle… Click to show full abstract

A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.

Keywords: phosphine catalyzed; coupling benzyl; halides fumarates; cross coupling; benzyl halides

Journal Title: Organic letters
Year Published: 2021

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