Regio- and Enantioselective Alkoxycarbonylation of Unactivated Terminal Alkenes under Palladium-Bromide-Monophosphine Catalysis.

Michel Sigrist, Kuhali Das, Gracjan Kurpik, Wei Tian, Jianxun Huang, Ala Covas, Andrew D Bond, Wenjun Tang, Paweł Dydio

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Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

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9 authors.

Michel SigristYusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.

Kuhali DasYusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.

Gracjan KurpikYusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.

Wei TianState Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

Jianxun HuangState Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

Ala CovasUniversity of Strasbourg, CNRS, ISIS UMR 7006, 67000 Strasbourg, France.

Andrew D BondYusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.ORCID 0000-0002-1744-0489

Wenjun TangState Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.ORCID 0000-0002-8209-4156

Paweł DydioYusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.ORCID 0000-0001-5095-4943

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Regio- and stereoselective hydrocarbonylation of unactivated alkenes, including abundant light olefins produced on a large scale and a diverse range of other commercial and synthetic materials, remains a formidable challenge in fine-chemical synthesis. Here, we report a highly regio- and enantioselective alkoxycarbonylation of a range of unactivated terminal olefins with a variety of alcohols, including biologically relevant motifs, to afford valuable chiral esters in typically >95:5 enantiomeric ratios, >95:5 regioisomeric ratios, and >80% yields. Chiral alcohols bearing adjacent stereogenic centers can be transformed into either diastereomer of the products with >92:8 diastereomeric ratios and >80% yields. Central to this method is a palladium-bromide catalyst featuring a newly developed valley-shaped monophosphorus ligand, ValleyPhos. The crystal structure of the precatalyst (ValleyPhos)PdBr

Identifiers

PMID42315478

DOI10.1021/jacs.6c10237

PMCPMC13339162

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