Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds

Pan Dang; Zhilei Zheng; Yun Liang

doi:10.1021/acs.joc.6b02943

Copper-Catalyzed C(sp³)-S Bond and C(sp²)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds

J Org Chem. 2017 Feb 17;82(4):2263-2268. doi: 10.1021/acs.joc.6b02943. Epub 2017 Feb 1.

Authors

Pan Dang¹, Zhilei Zheng¹, Yun Liang¹

Affiliation

¹ National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha, Hunan 410081, China.

PMID: 28118716
DOI: 10.1021/acs.joc.6b02943

Abstract

The sulfuration reaction of 2-(2-iodobenzoyl) substituted, or 2-(2-iodobenzyl) substituted 1,2,3,4-tetrahydroisoquinolines with potassium sulfide proceeded in the presence of copper catalysts to give tetrahydroisoquinoline-fused 1,3-benzothiazine scaffolds in moderate to appropriate yields. This protocol provided an efficient and simple strategy to construct the corresponding benzothiazine derivatives via formation of C(sp³)-S bond and C(sp²)-S bond, which the C-S bonds formed via different routes in this reaction (traditional cross-coupling reaction via the cleavage of C-I bond and oxidative cross-coupling reaction via C(sp³)-H bond functionalization).

Publication types

Research Support, Non-U.S. Gov't