Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles.

Jiang Nan, Xin Ren, Qiang Yan, Shilei Liu, Jing Wang, Yangmin Ma, Michal Szostak

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Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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0cells of the map it votes in

1citing papers in PubMed

1.8field-weighted citation impact, top 17% of its field

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1 citing paper in PubMed, 12 citations in OpenAlex.

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation.Molecules (Basel, Switzerland) · 2023
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5 · Who and what money

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7 authors at 2 institutions in 2 countries.

Jiang NanThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.ORCID https://orcid.org/0000-0001-5570-6834

Xin RenThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.

Qiang YanThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.

Shilei LiuThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.

Jing WangThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.

Yangmin MaThe Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China nanjiang@sust.edu.cn.

Michal SzostakDepartment of Chemistry, Rutgers University 73 Warren Street Newark New Jersey 07102 USA.ORCID https://orcid.org/0000-0002-9650-9690

Innovation Team (China) · CNRutgers, The State University of New Jersey · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Direct functionalization of the C(O)-N amide bond is one of the most high-profile research directions in the last few decades; however oxidative couplings involving amide bonds and functionalization of thioamide C(S)-N analogues remain an unsolved challenge. Herein, a novel hypervalent iodine-induced twofold oxidative coupling of amines with amides and thioamides has been established. The protocol accomplishes divergent C(O)-N and C(S)-N disconnection by the previously unknown Ar-O and Ar-S oxidative coupling and highly chemoselectively assembles the versatile yet synthetically challenging oxazoles and thiazoles. Employing amides instead of thioamides affords an alternative bond cleavage pattern, which is a result of the higher conjugation in thioamides. Mechanistic investigations indicate ureas and thioureas generated in the first oxidation as pivotal intermediates to realize the oxidative coupling. These findings open up new avenues for exploring oxidative amide and thioamide bond chemistry in various synthetic contexts.

Identifiers

PMID36970078

DOI10.1039/d3sc00301a

PMCPMC10034197

OpenAlexW4322580123

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LicenceCC BY-NC

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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.