Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

Qingjing Yang; Pui Ying Choy; Qingyang Zhao; Man Pan Leung; Hoi Shan Chan; Chau Ming So; Wing Tak Wong; Fuk Yee Kwong

doi:10.1021/acs.joc.8b01599

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

Qingjing Yang, Pui Ying Choy, Qingyang Zhao, Man Pan Leung, Hoi Shan Chan, Chau Ming So, Wing Tak Wong, Fuk Yee Kwong

Research output: Journal article publication › Journal article › Academic research › peer-review

34 Citations (Scopus)

Abstract

Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc) ₂ /MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

Original language	English
Pages (from-to)	11369-11376
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.8b01599
Publication status	Published - 21 Sept 2018

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b01599

Cite this

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title = "Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates",

abstract = " Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc) 2 /MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners. ",

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T1 - Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

AU - Yang, Qingjing

AU - Choy, Pui Ying

AU - Zhao, Qingyang

AU - Leung, Man Pan

AU - Chan, Hoi Shan

AU - So, Chau Ming

AU - Wong, Wing Tak

AU - Kwong, Fuk Yee

PY - 2018/9/21

Y1 - 2018/9/21

N2 - Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc) 2 /MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

AB - Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc) 2 /MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

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DO - 10.1021/acs.joc.8b01599

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SN - 0022-3263

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Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

Abstract

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