Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

Yu, Yongqi; Xia, Zhenhai; Wu, Qianlong; Liu, Da; Lin, Ying‐Chu; Xiao, Yuanjiu; Tan, Ze; Deng, Wei; Zhu, Gangguo

doi:10.1016/j.cclet.2020.09.020

Cited by 26 publications

(7 citation statements)

References 65 publications

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“…On the basis of previous reports and our preliminary mechanistic results, a plausible catalytic cycle is proposed (Scheme ). Initially, the active Rh(III) species I is generated from [Cp*RhCl 2 ] 2 in the presence of AgSbF 6 and KH 2 PO 4 .…”

Section: Results and Discussionmentioning

confidence: 86%

Rh(III)-Catalyzed C–H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

Zhao

Shen

et al. 2022

J. Org. Chem.

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A highly efficient Rh(III)-catalyzed C−H diamidation and diamidation/intramolecular cyclization of Niminopyridinium ylides with dioxazolones has been developed, providing diamidated products and benzoxazinone products in good to excellent yields. Notably, the tunable selectivity of this reaction can be controlled by simply switching the solvent and the temperature. This reaction features operational simplicity, a broad substrate scope, and a good functional group tolerance.

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Section: Results and Discussionmentioning

confidence: 86%

Rh(III)-Catalyzed C–H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

Zhao

Shen

et al. 2022

J. Org. Chem.

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“…In contrast, Zhu and co-workers 80 observed the [3 + 3] annulation product benzoxazinones 171 when the reaction of sulfoxonium ylides with dioxazolones 169 was carried out at a higher temperature in the absence of any base additive (Scheme 79). In contrast to other annulation reports, sulfoxonium ylides serve as C3 synthons.…”

Section: Sulfoxonium Ylide As a Directing Group In Transition Metal-c...mentioning

confidence: 98%

“…The reaction mechanism initiates with the C-H activation of sulfoxonium ylides to form a 5-membered cobaltacycle intermediate A. Coordination of dioxazolone with In contrast, Zhu and co-workers 80 observed the [3 + 3] annulation product benzoxazinones 171 when the reaction of sulfoxonium ylides with dioxazolones 169 was carried out at a higher temperature in the absence of any base additive (Scheme 79). In contrast to other annulation reports, sulfoxonium ylides serve as C3 synthons.…”

Section: Sulfoxonium Ylide As a Directing Group In Transition Metal-c...mentioning

confidence: 99%

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

2023

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“…Mechanistic studies revealed that the C−H activation is involved in the rate‐determining step. The proposed catalytic cycle is given in Scheme 47 [69] …”

Section: Directing‐group‐assisted C−h Amidation Reactionsmentioning

confidence: 99%

Recent Advances in Cobalt‐Catalyzed, Directing‐Group‐Assisted C−H Bond Amidation Reactions

Sunny

Karvembu

2021

Adv Synth Catal

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C−N bond formation reactions have garnered a lot of interest in recent years due to the predominance of nitrogen‐containing compounds in most pharmacological medications. Since traditional approaches have several limitations, the transition metal‐catalyzed C−H amidation/amination process has arisen as a more atom‐friendly option. Because there are so many distinct kinds of C−H bonds in organic molecules, selective amidation of C−H bonds has always been a challenge. In this scenario, the directing‐group‐assisted C−H amidation has received considerable attention, especially with inexpensive metal cobalt, due to its unique properties and efficiency. We summarize recent developments in cobalt‐catalyzed directing‐group‐aided C−H bond amidation reactions in this review. We briefly discuss the evolution of directing group preferences and their function in the site selection.

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Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

Cited by 26 publications

References 65 publications

Rh(III)-Catalyzed C–H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

Rh(III)-Catalyzed C–H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Recent Advances in Cobalt‐Catalyzed, Directing‐Group‐Assisted C−H Bond Amidation Reactions

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