ArticleChemical science
Palladium-Catalyzed Cross-Coupling of α-Bromocarbonyls and Allylic Alcohols for the Synthesis of α-Aryl Dicarbonyl Compounds.
Article in Chemical science. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent.RSC advances · 2023Article
- Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides.The Journal of organic chemistry · 2022Article
- Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.Chemical reviews · 2022Review
- C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysisChemical science · 2021Article
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Authors and funding
2 authors.
Funding
Abstract
The palladium-catalyzed coupling of olefins and organohalides is a versatile approach for synthesizing complex molecules from simple starting materials. We have developed a palladium-catalyzed coupling of α-bromocarbonyl compounds with allylic alcohols for the generation of acyclic aryl-substituted dicarbonyl compounds. The reaction proceeds via a tandem olefin insertion of an α-acyl radical followed by a 1,2-aryl migration. In addition to providing preliminary evidence for a free radical mediated mechanism, we demonstrate unprecedented levels of 1,3-stereoinduction for the 1,2-migration step.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.