Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 39, Pages 11901-11905Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706781
Keywords
alkylation; alkynes; cross-coupling; cross-electrophile coupling; homogeneous catalysis
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Funding
- NIH NIGMS [R01 GM097243]
- NSF [NSF DGE-1419118]
- Novartis
- Pfizer
- Boehringer Ingelheim
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A new method for the synthesis of terminal and internal alkynes from the nickel-catalyzed decarboxylative coupling of N-hydroxyphthalimide esters and bromoalkynes is presented. This reductive cross-electrophile coupling is the first to use a C(sp)-X electrophile, and appears to proceed via an alkynylnickel intermediate. The internal alkyne products are obtained in yields of 41-95% without the need for a photocatalyst, light, or a strong oxidant. The reaction displays a broad scope of carboxylic acid and alkyne coupling partners, and can tolerate an array of functional groups, including carbamate NH, halogen, nitrile, olefin, ketone, and ester moieties. Mechanistic studies suggest that this process does not involve an alkynylmanganese reagent and instead proceeds through nickel-mediated bond formation.
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