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2022 , Vol. 42 >Issue 11: 3721 - 3729

DOI: https://doi.org/10.6023/cjoc202206029

研究论文

碘化钾催化无保护8-氨基喹啉的选择性C(5)-芳基硫醚化和C(5),C(7)-双芳基硫醚化及吲哚C(2),C(3)-双芳基硫醚化反应

  • 吴豪志 ,
  • 罗田 ,
  • 姜建文 ,
  • 万结平
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  • 江西师范大学化学化工学院 南昌 330022

收稿日期: 2022-06-18

  修回日期: 2022-07-13

  网络出版日期: 2022-08-10

基金资助

国家自然科学基金(22161022)

收起

KI-Catalyzed Selective C(5)-Sulfenylation and C(5),C(7)-Disulfenylation of Unprotected 8-Aminoquinolines and the Indole C(2),C(3)-Disulfenylation

  • Haozhi Wu ,
  • Tian Luo ,
  • Jianwen Jiang ,
  • Jieping Wan
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  • College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022
*E-mail: ;

Received date: 2022-06-18

  Revised date: 2022-07-13

  Online published: 2022-08-10

Supported by

National Natural Science Foundation of China(22161022)

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摘要

报道了采用2.5 mol%碘化钾为唯一催化剂, 无需任何过渡金属催条件下无保护8-氨基喹啉的碳-氢甲芳基硫醚化反应. 有趣的是, 通过简单调控反应时间和介质可以实现选择性的C(5)-芳基硫醚化和C(5),C(7)-双芳基硫醚化. 在对二甲苯中反应12 h时为C(5)-芳基硫醚化. 另一方面, 延长反应时间至24 h并更换反应介质为甲苯则选择性地发生C(5),C(7)-双芳基硫醚化. 此外, 双芳基硫醚化反应可以扩展到吲哚类底物, 实现含2,3-二芳基硫醚结构的吲哚合成.

关键词： 碳-氢键官能化; 自由基; 8-氨基喹啉; 选择性; 芳基硫醚化

本文引用格式

吴豪志 , 罗田 , 姜建文 , 万结平 . 碘化钾催化无保护8-氨基喹啉的选择性C(5)-芳基硫醚化和C(5),C(7)-双芳基硫醚化及吲哚C(2),C(3)-双芳基硫醚化反应[J]. 有机化学, 2022 , 42(11) : 3721 -3729 . DOI: 10.6023/cjoc202206029

Abstract

The aromatic C—H sulfenylation reactions of unprotected 8-aminoquinolines have been realized by employing KI as the only catalyst at 2.5 mol% loading without using any transition metal reagent. Interestingly, the selective C(5)-sulfenylation and C(5),C(7)-disulfenylation have been successfully achieved by simply controlling the reaction time. Reaction time of 12 h in p-xylene enables the C(5)-sulfenylation. On the other hand, prolonging the reaction time to 24 h and switching the reaction medium to toluene lead to the selective C(5),C(7)-double sulfenylation. Moreover, the double sulfenylation has been extended to the indole substrate for the selective synthesis of 2,3-disulfenyl indoles.

Key words： C—H functionalization; free radical; 8-aminoquinoline; selectivity; sulfenylation

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