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PdII-Catalyzed Site-selective ß- and γ-C(sp3)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.
Li, Yi-Hao; Ouyang, Yuxin; Chekshin, Nikita; Yu, Jin-Quan.
Afiliação
  • Li YH; Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
  • Ouyang Y; Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
  • Chekshin N; Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
  • Yu JQ; Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
J Am Chem Soc ; 144(11): 4727-4733, 2022 03 23.
Article em En | MEDLINE | ID: mdl-35286807
Pd(II)-catalyzed site-selective ß- and γ-C(sp3)-H arylation of primary aldehydes is developed by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are identified to be crucial for the observed reactivity. By minimizing the loading of acid additives, the ligand effect is enhanced to achieve high reactivities of the challenging primary aldehyde substrates. Site selectivity can be switched from the proximate to the relatively remote position by changing the bite angle of TDG to match the desired palladacycle size. Experimental and computational investigations support this rationale for designing TDG to potentially achieve remote site-selective C(sp3)-H functionalizations.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Aldeídos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Aldeídos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Estados Unidos