Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes via Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes

被引：4

作者：

Gao, Yong ^{[1
]}

Hua, Ruirui ^{[1
]}

Yin, Hongquan ^{[1
,2
]}

Chen, Fu-Xue ^{[1
,2
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, Liangxiang Campus, Beijing 102488, Peoples R China

[2] Beijing Inst Technol, Minist Ind & Informat Technol, Key Lab Med Mol Sci & Pharmaceut Engn, Liangxiang Campus, Beijing 102488, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 11期

关键词：

ARYL THIOCYANATES; POLYCYCLIC AROMATICS; ORGANIC THIOCYANATES; REAGENT; TRANSFORMATION; DERIVATIVES; CYCLIZATION; DISULFIDES; CHEMISTRY; EFFICIENT;

D O I：

10.1039/d3ob00001j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem electrophilic thiocyanation and cyclization of arene-alkynes has been developed under mild conditions, affording thiocyanato-substituted phenanthrenes, dihydronaphthalenes, 2H-chromenes and dihydroquinolines in moderate to excellent yields. This reaction provides an efficient protocol for the construction of C-SCN and C-C bonds in one step. In this transformation, N-thiocyanato reagent serves as a convenient precursor to transfer SCN+ in the presence of trimethylchlorosilane, and the cyclization exhibited exclusive 6-endo-dig selectivity. Finally, a gram scale reaction and further derivatizations highlight the utility of this synthetic strategy.

引用

页码：2417 / 2422

页数：6

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