Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate

被引：119

作者：

Ghosh, Koushik ^{[1
]}

Nishii, Yuji ^{[2
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers, Suita, Osaka 5650871, Japan

来源：

ACS CATALYSIS | 2019年 / 9卷 / 12期

关键词：

rhodium; C-H functionalization; acetylene; cyclization; N-heterocycles; C-H ACTIVATION; INTERNAL ALKYNES; OXIDATIVE COUPLING/CYCLIZATION; BOND; INDOLES; ISOQUINOLONES; ALKALOIDS; STRATEGY; ANILINES; ACCESS;

D O I：

10.1021/acscatal.9b04254

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Transition-metal-catalyzed C-H activation and subsequent oxidative cyclization with alkynes has been a powerful tool for the synthesis of polycyclic aromatic compounds. Despite the substantial progress in this field, it is still a significant challenge to establish synthetic methodologies for the construction of non substituted vinylene-fused aromatics. We herein report a Rh(III)-catalyzed C-H/N-H annulation with vinylene carbonate as an acetylene surrogate. Vinylene carbonate also acts as an internal oxidant to regenerate the Rh(III) species in situ; thus, no external oxidant is required to trigger the oxidative annulation. This protocol is applicable to the direct synthesis of various N-heteroaromatics.

引用

页码：11455 / 11460

页数：11

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