Publication

Palladium-catalysed cross-coupling of lithium acetylides

Helbert, H., Visser, P., Hermens, J. G. H., Buter, J. & Feringa, B. L., Aug-2020, In : Nature Catalysis. 3, 8, p. 664-671 8 p.

Research output: Contribution to journalArticleAcademicpeer-review

The incorporation of alkynes into organic molecules is one of the most valuable transformations for the formation of C–C bonds and provides a versatile handle for further modifications. The Sonogashira cross-coupling of acetylenes holds a prominent position among the suite of catalytic cross-coupling reactions that are key to modern synthesis. Here we present a method that is complementary to the Sonogashira reaction, demonstrating cross-coupling of lithium acetylides with aryl bromides. The reactions take place under ambient conditions with short reaction times, affording the corresponding aryl acetylenes in good to excellent yields while displaying a remarkable functional group tolerance for an organolithium reaction, allowing the presence of a variety of organolithium-sensitive carbonyl functionalities. This developed cross-coupling methodology offers ample opportunities to access a wide variety of acetylenes, as is illustrated by the facile preparation of key intermediates for chemical biology and optoelectronic materials. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)664-671
Number of pages8
JournalNature Catalysis
Volume3
Issue number8
Publication statusPublished - Aug-2020

    Keywords

  • ONE-POT CONVERSION, DERIVATIVES, REACTIVITY, LITHIATION, ACIDITIES, ALDEHYDES, KETONES, ALKYNES, DESIGN, SCALE

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