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Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes via Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes.
Org Biomol Chem. 2023 Mar 15; 21(11):2417-2422.OB

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Gao Y
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China. fuxue.chen@bit.edu.cn.
Hua R
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China. fuxue.chen@bit.edu.cn.
Yin H
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China. fuxue.chen@bit.edu.cn. Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
Chen FX
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China. fuxue.chen@bit.edu.cn. Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36857671

Citation

Gao, Yong, et al. "Synthesis of Thiocyanato-containing Phenanthrenes and Dihydronaphthalenes Via Lewis Acid-activated Tandem Electrophilic Thiocyanation/carbocyclization of Alkynes." Organic & Biomolecular Chemistry, vol. 21, no. 11, 2023, pp. 2417-2422.
Gao Y, Hua R, Yin H, et al. Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes via Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes. Org Biomol Chem. 2023;21(11):2417-2422.
Gao, Y., Hua, R., Yin, H., & Chen, F. X. (2023). Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes via Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes. Organic & Biomolecular Chemistry, 21(11), 2417-2422. https://doi.org/10.1039/d3ob00001j
Gao Y, et al. Synthesis of Thiocyanato-containing Phenanthrenes and Dihydronaphthalenes Via Lewis Acid-activated Tandem Electrophilic Thiocyanation/carbocyclization of Alkynes. Org Biomol Chem. 2023 Mar 15;21(11):2417-2422. PubMed PMID: 36857671.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR 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, Y1 - 2023/03/15/ PY - 2023/3/2/pubmed PY - 2023/3/2/medline PY - 2023/3/1/entrez SP - 2417 EP - 2422 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 21 IS - 11 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/36857671/Synthesis_of_thiocyanato_containing_phenanthrenes_and_dihydronaphthalenes_via_Lewis_acid_activated_tandem_electrophilic_thiocyanation/carbocyclization_of_alkynes_ DB - PRIME DP - Unbound Medicine ER -
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