Synthesis of allenynes via Pd-catalyzed coupling of 1,4-diyn-3-yl carbonates with boronic acids
Literature Information
Publication Date
2023-11-22
DOI
10.1039/D3QO01648J
Impact Factor
5.281
Authors
Jie Wang, Hui Qian
View Original
Abstract
Conjugated allenynes widely exist in natural products and are commonly employed in the development of functional materials. However, synthetic methods are very limited. In this contribution, a palladium-catalyzed cross-coupling reaction of 1,4-diyn-3-yl carbonates with a series of commercially available boronic acids using S-phos or Gorlos-phos as the ligand has been developed. Diversely substituted allenynes incorporating synthetically useful functional groups are obtained in good yields under this set of mild conditions. Gram-scale reactions and synthetic transformations have been conducted to show their potential utility.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 2-carbamimidoyl-1-piperidinecarboxylate
CAS Number:
1258640-98-0
Molecular Formula:
C11H21N3O2
![N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure](https://static.chemtradehub.com/structs/210/2101206-92-0-2eb5.webp "N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure")
N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide
CAS Number:
2101206-92-0
Molecular Formula:
C20H30N2O10
(2R)-2-(3-Bromophenyl)pyrrolidine hydrochloride (1:1)
CAS Number:
1391550-13-2
Molecular Formula:
C10H13BrClN
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