ArticleNature communications2019
Sulfenamide-enabled ortho thiolation of aryl iodides via palladium/norbornene cooperative catalysis.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 72 citations in OpenAlex.
- Meta-Dimethylation of Arenes via Catellani Reaction from Aryl Thianthrenium Salts.Angewandte Chemie (International ed. in English) · 2025Article
- Aryl ortho methoxylation.Nature chemistry · 2023Article
- Ortho-C-H methoxylation of aryl halides enabled by a polarity-reversed N-O reagent.Nature chemistry · 2023Article
- Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.Chemical science · 2022Article
- Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.Angewandte Chemie (International ed. in English) · 2021Article
- Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2020Review
- Article
- UnexpectedOrganic letters · 2020Article
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Authors and funding
5 authors at 3 institutions in 1 country.
Funding
Abstract
Poly-substituted aromatic sulfur compounds are widely found in pharmaceuticals, agrochemicals and organic materials. However, the position that a sulfur moiety can be introduced to is largely restricted to a pre-functionalized site; otherwise, use of electronically biased substrates or auxiliary groups that direct catalysis is required. Here we report a general ortho thiolation of common aryl and heteroaryl iodides via palladium-norbornene cooperative catalysis. Using this approach, an aryl or alky sulfur moiety can be site-selectively introduced at the arene ortho position without using sterically or electronically biased substrates. The arene ipso functionalization is simultaneously achieved through Heck, Suzuki or Sonogashira termination. The reaction is enabled by a unique class of electrophiles in palladium-norbornene cooperative catalysis, which are sulfenamides derived from seven-membered lactams. The broad substrates scope and high chemoselectivity could make this method attractive for synthesis of complex sulfur-containing aromatic compounds.
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