Comprehensive Strategies for the Synthesis of 1,3-Enyne Derivatives

Abstract

The synthesis of 1,3-enyne has widespread appeal in organic synthesis due to their proven adaptability as intermediates in routes to compounds of significant biological and material interest. A variety of methods have been designed to formulate 1,3-enynes from diverse substrates, such as alkynes, 1,3-diynes, alkynyl-substituted cyclopropanes, and propargyl alcohols. This review covers the synthesis of 1,3-enynes utilizing the homo- and cross-coupling of alkynes, nucleophilic metal/acid-induced cyclopropane ring opening, and rearrangement/dehydration of propargyl alcohols. A key concern in procedures starting from alkynes and 1,3-diynes is the management of regio-, stereo-, and, where fitting, chemoselectivity. In contrast, in cyclopropyl ring opening nucleophile orientation determines the 1,3-enynes formed. Efficient methods for the broad and selective synthesis of 1,3-enynes are highlighted and specific examples are given to demonstrate the efficacy of these processes.

1 Introduction and Scope

2 Synthesis

2.1 Synthesis of 1,3-Enynes from Alkynes

2.1.1 Metal-Catalyzed Cross-Coupling/Additions of Alkynes with Alkenes or Vinyl or Aryl Halides

2.1.1.1 Palladium Catalysis

2.1.1.2 Rhodium Catalysis

2.1.1.3 Copper Catalysis

2.1.1.4 I ron Catalysis

2.1.1.5 Nickel Catalysis

2.1.1.6 Miscellaneous

2.2 Synthesis of Enynes from Propargyl Alcohols

2.3 Metal/Acid-Catalyzed Ring Opening of Cyclopropanes

3 Conclusion

Key words

alkynes precursors - acid catalysis - coupling reactions - enyne synthesis - metal-catalysis

Publication History

Received: 28 March 2024

Accepted after revision: 01 May 2024

Accepted Manuscript online:
01 May 2024

Article published online:
10 June 2024

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