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Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.
J Am Chem Soc. 2020 02 12; 142(6):2715-2720.JA

Abstract

A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic cis-olefins are suitable substrates, and the reaction is operated under air with excellent site-selectivity. Preliminary mechanistic studies are consistent with the proposed Pd/NBE-catalyzed C-H activation instead of the Heck pathway. Initial success on distal alkylation has also been achieved using MeI and methyl bromoacetate as electrophiles.

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Authors+Show Affiliations

Wu Z
Department of Chemistry , University of Chicago , Chicago , Illinois 60637 , United States.
Fatuzzo N
Department of Chemistry , University of Chicago , Chicago , Illinois 60637 , United States.
Dong G
Department of Chemistry , University of Chicago , Chicago , Illinois 60637 , United States.

MeSH

AlkenesAlkylationCatalysisMolecular StructureNorbornanesPalladiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

31995370

Citation

Wu, Zhao, et al. "Distal Alkenyl C-H Functionalization Via the Palladium/Norbornene Cooperative Catalysis." Journal of the American Chemical Society, vol. 142, no. 6, 2020, pp. 2715-2720.
Wu Z, Fatuzzo N, Dong G. Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis. J Am Chem Soc. 2020;142(6):2715-2720.
Wu, Z., Fatuzzo, N., & Dong, G. (2020). Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis. Journal of the American Chemical Society, 142(6), 2715-2720. https://doi.org/10.1021/jacs.9b11479
Wu Z, Fatuzzo N, Dong G. Distal Alkenyl C-H Functionalization Via the Palladium/Norbornene Cooperative Catalysis. J Am Chem Soc. 2020 02 12;142(6):2715-2720. PubMed PMID: 31995370.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis. AU - Wu,Zhao, AU - Fatuzzo,Nina, AU - Dong,Guangbin, Y1 - 2020/02/03/ PY - 2020/1/30/pubmed PY - 2021/1/20/medline PY - 2020/1/30/entrez SP - 2715 EP - 2720 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 142 IS - 6 N2 - A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic cis-olefins are suitable substrates, and the reaction is operated under air with excellent site-selectivity. Preliminary mechanistic studies are consistent with the proposed Pd/NBE-catalyzed C-H activation instead of the Heck pathway. Initial success on distal alkylation has also been achieved using MeI and methyl bromoacetate as electrophiles. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/31995370/Distal_Alkenyl_C_H_Functionalization_via_the_Palladium/Norbornene_Cooperative_Catalysis_ DB - PRIME DP - Unbound Medicine ER -