Aromatization of cyclic hydrocarbons <i>via</i> thioether elimination reaction

Liu, Yang; Feng, Yingqi; Nie, Jinli; Xie, Sijie; Pen, Xin; Hong, Huanliang; Chen, Xiuwen; Chen, Lu; Li, Yibiao

doi:10.1039/d3cc03279e

“…The authors have cited additional references within the Supporting Information. [28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]…”

Section: Supporting Informationmentioning

confidence: 99%

Meta‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Guo,

Xu,

Studer

2024

Angew Chem Int Ed

4

0

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C(sp2)–H functionalization offers an efficient strategy for the synthesis of various elaborated N‐containing heteroarenes. Along these lines, oxazino pyridines that can be readily prepared from pyridines, have been introduced as powerful substrates in radical‐ and ionic‐mediated meta‐C–H functionalization. However, the regioselective meta‐C–H arylation of pyridines remains a great challenge. Herein, a copper‐catalyzed meta‐selective C–H arylation of pyridines and isoquinolines through bench‐stable dearomatized intermediates is reported. Electrophilic aryl‐Cu(III) species, generated from readily accessible aryl I(III) reagents, enable the efficient meta‐arylation of a broad range of pyridines and isoquinolines. The method also allows the meta‐selective alkenylation of these heteroarenes using the corresponding alkenyl I(III)‐reagents. Late‐stage arylation of drug‐derived pyridines and larger‐scale experiments demonstrate the potential of this synthetic methodology.

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“…Compared with Lawesson's reagent, xanthate is widely available, safe, stable, and nontoxic (Scheme 1c). Based on our research on the development of xanthate chemistry, 23 herein, we report a facile approach to obtain various thiols, disulfides, and thioesters that involves the reductive sulfuration of aryl aldehydes using EtOCS 2 K without a reducing agent (Scheme 1d).…”

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confidence: 99%

Potassium xanthate-promoted reductive sulfuration reaction: from aldehydes to thiol, disulfide, and thioester derivatives

Feng,

Nie,

Xie

et al. 2024

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Meta‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Guo,

Xu,

Studer

2024

Angewandte Chemie

0

View full text Add to dashboard Cite

C(sp2)–H functionalization offers an efficient strategy for the synthesis of various elaborated N‐containing heteroarenes. Along these lines, oxazino pyridines that can be readily prepared from pyridines, have been introduced as powerful substrates in radical‐ and ionic‐mediated meta‐C–H functionalization. However, the regioselective meta‐C–H arylation of pyridines remains a great challenge. Herein, a copper‐catalyzed meta‐selective C–H arylation of pyridines and isoquinolines through bench‐stable dearomatized intermediates is reported. Electrophilic aryl‐Cu(III) species, generated from readily accessible aryl I(III) reagents, enable the efficient meta‐arylation of a broad range of pyridines and isoquinolines. The method also allows the meta‐selective alkenylation of these heteroarenes using the corresponding alkenyl I(III)‐reagents. Late‐stage arylation of drug‐derived pyridines and larger‐scale experiments demonstrate the potential of this synthetic methodology.

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Aromatization of cyclic hydrocarbons via thioether elimination reaction

Abstract: Herein, the diversity-oriented aromatization of cyclic hydrocarbons via potassium ethyl xanthogenate (EtOCS2K)/NH4I-mediated methylthiyl radical addition and thioether elimination was investigated under transition-metal-free conditions. The methylthiyl radical species were generated in...

Cited by 4 publications

References 62 publications

Meta‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Meta‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

Potassium xanthate-promoted reductive sulfuration reaction: from aldehydes to thiol, disulfide, and thioester derivatives

Meta‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates

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