Synthesis of 6-(Arylthio)phenanthridines by Copper-Catalyzed Tandem Reactions of 2-Biaryl Isothiocyanates with Diaryliodonium Salts

Guo, Wei‐Si; Li, Shoulei; Tang, Lin; Li, Ming; Wen, Li‐Rong; Chen, Chao

doi:10.1021/acs.orglett.5b00197

Cited by 61 publications

(23 citation statements)

References 73 publications

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“…Chen and co‐workers in 2015 developed [37] a copper‐mediated tandem C−S/C−C arylation‐cyclization reaction for the construction of 6‐(arylthio)phenanthridines 111 from 2‐biaryl isothiocyanates 109 and diaryliodonium salts 110 under mild conditions. This is the first general synthetic route to construct phenanthridines 111 from 2‐biaryl isothiocyanates 109 .…”

Section: Synthesis Of Phenanthridinesmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds. There has been considerable scientific interest in the turn of this century in the synthesis of these N‐containing heterocycles as they are prevalent in many alkaloids and also possess striking biological activities including antibacterial, antifungal, antitumor activities. In this regard, a number of synthetic approaches toward the construction of phenanthridine moieties with various substituents, and to increase their yield have been developed by the synthetic organic community. Even though many researchers have developed various innovative methods for the synthesis of phenanthridine derivatives for the past few years, still there is substantial scope for the discovery of novel synthetic methods. In this review, the latest developments in the diverse synthetic strategies of phenanthridine derivatives in the presence and absence of metals were described. The present review also enlightens the use of different reagents, the diversity of the substrates identified, and the plausible mechanisms unravelled towards the construction of these biologically relevant scaffolds.

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Section: Synthesis Of Phenanthridinesmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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“…In analogy with their previously reported cascade annulation reactions of nitriles and diaryliodonium salts, [70][71][72][73] Chen and co-workers reported a copper-catalyzed synthesis of 6-(arylthio)phenanthridines 192 from 2-biaryl isothiocyanates 191. 94 This transformation used CuCl as catalyst and involved an initial arylation of the sulfur atom of the isothiocyanate group and a subsequent cyclization via intramolecular trapping of the resulting sulfonium intermediate (Scheme 61). Control experiments with unsymmetrical diaryliodonium salts, in which the less sterically hindered or the more electron-rich aryl group was selectively transferred at the sulfur atom, indicated that an aryl carbocation rather than an aryl radical was involved in this reaction.…”

Section: Scheme 60mentioning

confidence: 99%

Copper-Catalyzed Arylation with Diaryliodonium Salts

Fañanás‐Mastral

2017

Synthesis

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The unique reactivity of diaryliodonium salts with copper complexes has been applied to a variety of synthetic organic transformations. These hypervalent iodine compounds have been used for diverse copper-catalyzed cross-coupling reactions including C-H functionalizations, enantioselective CC bond formation, cascade reactions and different heteroatom arylation processes. This review provides a summary of recent developments on this topic and discusses both the synthetic utility and mechanisms of these transformations.

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“…In an elegant report in 2013, Chen and co‐workers described a highly regioselective [2+2+2] cyclization of diaryliodonium salts, alkynes, and nitriles promoted by catalytic amounts of Cu(OTf) 2 (Scheme a) . Later, the same group has developed a novel synthesis of 6‐(arylthio)phenanthridines by using a Cu‐catalyzed S ‐arylation of 2‐biaryl isothiocyanates (Scheme b) . The reactivity of aryl–Cu III species with other isothiocyanates was extensively studied by Li et al Very recently, they presented a novel synthesis of thiochromeno[2,3‐ b ]indoles from 2‐alkynylaryl isothiocyanates and iodonium salts (Scheme c) .…”

Section: Figurementioning

confidence: 99%

Cu‐catalyzed Cascade Cyclization of Isothiocyanates, Alkynes, and Diaryliodonium Salts: Access to Diversely Functionalized Quinolines

Khan

Volla

2017

Chemistry A European J

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Herein, we report a copper-catalyzed novel, highly efficient, and modular cascade annulation reaction for the synthesis of quinoline derivatives starting from easily available alkynes, isothiocyanates, and diaryliodonium salts. The reaction displayed excellent regioselectivities, when unsymmetrical alkynes were employed as partners, giving access to diversely functionalized quinolines in good to excellent yields for a wide range of functional groups.

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Synthesis of 6-(Arylthio)phenanthridines by Copper-Catalyzed Tandem Reactions of 2-Biaryl Isothiocyanates with Diaryliodonium Salts

Cited by 61 publications

References 73 publications

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Copper-Catalyzed Arylation with Diaryliodonium Salts

Cu‐catalyzed Cascade Cyclization of Isothiocyanates, Alkynes, and Diaryliodonium Salts: Access to Diversely Functionalized Quinolines

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