ArticleJournal of the American Chemical Society2015
Monoselective o-C-H Functionalizations of Mandelic Acid and α-Phenylglycine.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Article
- Ligand-Enabled C-H Hydroxylation with Aqueous HJournal of the American Chemical Society · 2022Article
- Pd-catalysed C-H functionalisation of free carboxylic acids.Chemical science · 2022Review
- Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.Chemical science · 2021Review
- Ligand-Enabled Monoselective β-C(spJournal of the American Chemical Society · 2020Article
- Pd-catalyzed site-selective C(spChemical science · 2019Article
- An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl.Molecules (Basel, Switzerland) · 2019Article
- A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.Chemical Society reviews · 2018Review
- Ligand-enabledChemical science · 2018Article
- Ligand-Enabled Auxiliary-Free meta-C-H Arylation of Phenylacetic Acids.Angewandte Chemie (International ed. in English) · 2017Article
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Authors and funding
4 authors.
Funding
Abstract
Pd-catalyzed C-H functionalization of mandelic acid and α-phenylglycine is reported. We have developed different protocols for the arylation, iodination, acetoxylation, and olefination of these substrates based on two different (Pd(II)/Pd(IV) and Pd(II)/Pd(0)) catalytic cycles. Four crucial features of these protocols are advantageous for practical applications. First, the α-hydroxyl and amino groups are protected with simple protecting groups such as acetates (Ac, Piv) and carbamates (Boc, Fmoc), respectively. Second, these protocols do not involve installation and removal of a directing group. Third, monoselectivity is accomplished. Fourth, no epimerization occurs at the vulnerable α-chiral centers.
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