ArticleAngewandte Chemie (International ed. in English)2020
Rational Development of Remote C-H Functionalization of Biphenyl: Experimental and Computational Studies.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 50 citations in OpenAlex.
- Construction of axial chirality through addressing theChemical science · 2026Article
- From Mono-Accounts of chemical research · 2025Review
- Hydrogen bonding template enables remote meta-C-H alkenylation of nitroarenes with electron-deficient alkenes.Nature communications · 2024Article
- MacrocyclizationChemical science · 2023Article
- Palladium-CatalyzedACS catalysis · 2022Article
- Pd(ii)-catalyzedChemical science · 2022Article
- Atropoenantioselective palladaelectro-catalyzed anilide C-H olefinations viable with natural sunlight as sustainable power source.Chemical science · 2022Article
- Stereoselective rhodium-catalyzed 2-C-H 1,3-dienylation of indoles: dual functions of the directing group.Chemical science · 2021Article
- Recent development in transition metal-catalysed C-H olefination.Chemical science · 2021Review
- Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with OScience (New York, N.Y.) · 2020Article
- meta-Selective C-H Arylation of Fluoroarenes and Simple Arenes.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
Abstract
A simple and efficient nitrile-directed meta-C-H olefination, acetoxylation, and iodination of biaryl compounds is reported. Compared to the previous approach of installing a complex U-shaped template to achieve a molecular U-turn and assemble the large-sized cyclophane transition state for the remote C-H activation, a synthetically useful phenyl nitrile functional group could also direct remote meta-C-H activation. This reaction provides a useful method for the modification of biaryl compounds because the nitrile group can be readily converted to amines, acids, amides, or other heterocycles. Notably, the remote meta-selectivity of biphenylnitriles could not be expected from previous results with a macrocyclophane nitrile template. DFT computational studies show that a ligand-containing Pd-Ag heterodimeric transition state (TS) favors the desired remote meta-selectivity. Control experiments demonstrate the directing effect of the nitrile group and exclude the possibility of non-directed meta-C-H activation. Substituted 2-pyridone ligands were found to be key in assisting the cleavage of the meta-C-H bond in the concerted metalation-deprotonation (CMD) process.
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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.