Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

University of Ontario Institute of Technology (UOIT) 2000 Simcoe Street North, Oshawa, Ontario, Canada L1H 7K4

Org. Lett., 2014, 16 (2), pp 488–491

DOI: 10.1021/ol403370t

Publication Date (Web): December 18, 2013

Abstract

A straightforward method for the preparation of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without exclusion of air and moisture.

Supporting Information

Experimental procedures and characterization data for organotrifluoroborate salts and compounds 1a–m, 2a–c, 3a–c, 4a, and 5a. This material is available free of charge via the Internet at http://pubs.acs.org.

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Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Letter

Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Abstract

Supporting Information

PDF

Proofs

Interrupting Nazarov Reaction with Different Trapping Modality: Utilizing Potassium Alkynyltrifluoroborate as a σ-Nucleophile

Brønsted Acid-Catalyzed Reactions of Trifluoroborate Salts with Benzhydryl Alcohols

A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide

Phosphinito palladium( ii ) complexes as catalysts for the synthesis of 1,3-enynes, aromatic alkynes and ynones

Synthesis of Iron Oxide Palladium Nanoparticles and Their Catalytic Applications for Direct Coupling of Acyl Chlorides with Alkynes

Synthesis of Fluorescent 1,3-Diarylpropynones by Carbonylative Alkynylation Reaction Using (Phosphine) (1,2,3-triazol-5-ylidene)palladium Complexes as Catalysts

Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts

Highly efficient transition metal-free coupling of acid chlorides with terminal alkynes in [bmim]Br: A rapid route to access ynones using MgCl2

Palladium anchored on amine-functionalized K10 as an efficient, heterogeneous and reusable catalyst for carbonylative Sonogashira reaction

A General Access to Propargylic Ethers through Brønsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

Metal-free synthesis of ynones via direct C–H alkynylation of aldehydes with ethynylbenziodoxolones

Photoinduced Synthesis of P -Perfluoroalkylated Phosphines from Triarylphosphines and Their Application in the Copper-Free Cross-Coupling of Acid Chlorides and Terminal Alkynes

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A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents

Rh( iii )- or Ir( iii )-catalyzed ynone synthesis from aldehydes via chelation-assisted C–H bond activation

Palladium-catalyzed carbonylative Sonogashira coupling between aryl triazenes and alkynes

Metal-free carbonyl C(sp 2 )–H oxidative alkynylation of aldehydes using hypervalent iodine reagents leading to ynones

Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

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Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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