A combined experimental and computational study of ligand-controlled Chan-Lam coupling of sulfenamides.

Kaiming Han, Hong Liu, Madeline E Rotella, Zeyu Xu, Lizhi Tao, Shufeng Chen, Marisa C Kozlowski, Tiezheng Jia

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Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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8 authors.

Kaiming Han *Research Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen, Guangdong, P. R. China.

Hong Liu *Research Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen, Guangdong, P. R. China.

Madeline E Rotella *Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania, USA.

Zeyu XuResearch Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen, Guangdong, P. R. China.

Lizhi TaoResearch Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen, Guangdong, P. R. China.ORCID http://orcid.org/0000-0001-9921-2297

Shufeng ChenInner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, P. R. China. shufengchen@imu.edu.cn.ORCID http://orcid.org/0000-0002-7021-2581

Marisa C KozlowskiRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania, USA. marisa@sas.upenn.edu.ORCID http://orcid.org/0000-0002-4225-7125

Tiezheng JiaResearch Center for Chemical Biology and Omics Analysis, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen, Guangdong, P. R. China. jiatz@sustech.edu.cn.ORCID http://orcid.org/0000-0002-9106-2842

Funding

Computation and Development of New, Enabling Synthetic MethodsR35GM131902 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI Marisa C Kozlowski · 2019 to 2026

$4.5M

NIGMS NIH HHS R35 GM131902

6 · The paper itself

Abstract

The unique features of the sulfenamides' S(II)-N bond lead to interesting stereochemical properties and significant industrial functions. Here we present a chemoselective Chan-Lam coupling of sulfenamides to prepare N-arylated sulfenamides. A tridentate pybox ligand governs the chemoselectivity favoring C-N bond formation, and overrides the competitive C-S bond formation by preventing the S,N-bis-chelation of sulfenamides to copper center. The Cu(II)-derived resting state of catalyst is captured by UV-Vis spectra and EPR technique, and the key intermediate is confirmed by the EPR isotope response using

Identifiers

PMID38834552

DOI10.1038/s41467-024-49089-0

PMCPMC11150460

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