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Synthesis 2025; 57(01): 39-70
DOI: 10.1055/a-2317-7262
DOI: 10.1055/a-2317-7262
review
Special Topic Dedicated to Prof. H.Ila
Comprehensive Strategies for the Synthesis of 1,3-Enyne Derivatives
Authors
C.C.M. appreciates the Science and Engineering Research Board (Grant Nos. CRG/2020/004509 and ECR/2016/000337), Ministry of Education, India, STARS, IISc Bangalore (STARS/STARS-2/2023-0928), and National Institute of Technology Manipur for financial support. K.K. and C.K.P are grateful to the Ministry of Education, India for fellowship support.
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-catalysisPublikationsverlauf
Eingereicht: 28. März 2024
Angenommen nach Revision: 01. Mai 2024
Accepted Manuscript online:
01. Mai 2024
Artikel online veröffentlicht:
10. Juni 2024
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