Iodine-Promoted Tunable Synthesis of 2-Naphthyl Thioethers and 1-Naphthyl Thioethers

被引：12

作者：

Bao, Yishu ^{[1
]}

Yang, Xiuqin ^{[1
]}

Dai, Zonghao ^{[1
]}

Ji, Suyu ^{[1
]}

Zhou, Qingfa ^{[1
]}

Yang, Fulai ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Tetralones; Disulfides; Iodine; Deoxygenation; Synthetic methods; ARYL CHLORIDES; BORONIC ACIDS; SULFIDES; THIOLS; METHYLTHIOLATION; SULFENYLATION; ARYLATION; CARBON;

D O I：

10.1002/adsc.201801562

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An iodine-promoted regioselective sulfenylation/deoxygenation/aromatization reaction of 1-tetralones with disulfides has been developed. This process could be modified to synthesize 2-naphthyl thioethers and 1-naphthyl thioethers in moderate to excellent yields, respectively. Furthermore, when the reaction was extended to 2-tetralones, 2-naphthyl thioethers were obtained as the sole products. The current study bridges the deoxygenation and sulfenylation/aromatization of ketones, thus providing a new tool in organic synthesis.

引用

页码：2154 / 2158

页数：5

共 48 条

[11] CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chloridess
Chen, Chia-Wei
Chen, Yi-Ling
Reddy, Daggula Mallikarjuna
Du, Kai
Li, Chao-En
Shih, Bo-Hao
Xue, Yung-Jing
Lee, Chin-Fa
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (42) : 10087 - 10091
[12] Clemmensen E., 1914, CHEM BER, V47, P681
[13] Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes
Denmark, Scott E.
Rossi, Sergio
Webster, Matthew P.
Wang, Hao
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (37) : 13016 - 13028
[14] Zinc-Mediated Palladium-Catalyzed Formation of Carbon-Sulfur Bonds
Eichman, Chad C.
Stambuli, James P.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 4005 - 4008
[15] Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols
Fernandez-Rodriguez, Manuel A.
Shen, Qilong
Hartwig, John F.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) : 7782 - 7796
[16] Iodine-Catalyzed Selective Synthesis of 2-Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides
Ge, Wenlei
Zhu, Xun
Wei, Yunyang
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 3014 - 3021
[17] A convenient method for the synthesis of aryl methyl sulfides via Cu(I)-mediated methylthiolation of haloarenes with DMSO
Ghosh, Ketaki
Ranjit, Sadananda
Mal, Dipakranjan
[J]. TETRAHEDRON LETTERS, 2015, 56 (37) : 5199 - 5202
[18] Silver Ion Mediated In Situ Synthesis of Mixed Diaryl Sulfides from Diaryl Disulfides
Gogoi, Prasanta
Gogoi, Sandhya R.
Kalita, Mukul
Barman, Pranjit
[J]. SYNLETT, 2013, 24 (07) : 873 - 877
[19] Calix[8]arene nanoreactor for Cu(I)-catalysed C-S coupling
Guzman-Percastegui, Edmundo
Hernandez, David J.
Castillo, Ivan
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (15) : 3111 - 3114
[20] Huang M., 1946, J AM CHEM SOC, V68, P2487

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