Angewandte Chemie · 2017 · 49 citations · 58 references
Natural SciencesChemical EngineeringChemistryBiocatalysisCatalysisOrganic ChemistryCarboxylic DerivativesCatalytic MechanismsCross-coupling ReactionsOrganic SynthesisActivation Of Carboxylic AcidsAlkyne ActivationAlkyne Coupling ReactionsCarboxylic Acid SynthesisCatalytic IntermediatesDecarboxylative CouplingDecarboxylative Cross-couplingTransition-metal-catalyzed Cross-coupling
Abstract The development of a new decarboxylative cross‐coupling method that affords terminal and substituted alkynes from various carboxylic acids is described using both nickel‐ and iron‐based catalysts. The use of N‐hydroxytetrachlorophthalimide (TCNHPI) esters is crucial to the success of the transformation, and the reaction is amenable to in situ carboxylic acid activation. Additionally, an inexpensive, commercially available alkyne source is employed in this formal homologation process that serves as a surrogate for other well‐established alkyne syntheses. The reaction is operationally simple and broad in scope while providing succinct and scalable avenues to previously reported synthetic intermediates.
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An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes
S. Müller, Bernd Liepold, Gerald J. Roth et al. · Synlett · 1996 · 776 citations
A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents
Tian Qin, Josep Cornellà, Chao Li et al. · Science · 2016 · 744 citations