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

Yong Gao; Ruirui Hua; Hongquan Yin; Fu Xue Chen

doi:10.1039/d3ob00001j

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

Yong Gao, Ruirui Hua, Hongquan Yin, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2417-2422
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	11
DOIs	https://doi.org/10.1039/d3ob00001j
Publication status	Published - 1 Mar 2023

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

abstract = "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.",

author = "Yong Gao and Ruirui Hua and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

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doi = "10.1039/d3ob00001j",

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T1 - Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes via Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes

AU - Gao, Yong

AU - Hua, Ruirui

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2023/3/1

Y1 - 2023/3/1

N2 - 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.

AB - 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.

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DO - 10.1039/d3ob00001j

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SN - 1477-0520

VL - 21

SP - 2417

EP - 2422

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

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

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