期刊
ACS CATALYSIS
卷 11, 期 11, 页码 6357-6362出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01457
关键词
gold; pyrroles; nitrenoid; annulation; thioether; indole
资金
- EPSRC
- Eli Lilly [EP/R512436/1]
- European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant [839037]
- Royal Society
- Leverhulme Trust [SRF\R1\191033]
- Centre for Chemical and Materials Analysis in the School of Chemistry (UoB)
- Marie Curie Actions (MSCA) [839037] Funding Source: Marie Curie Actions (MSCA)
The research demonstrates the controlled access to (3+2) annulation by Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers, resulting in the synthesis of sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety. This offers a new strategy for achieving varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes.
The combination of nucleophilic nitrenoids and pacid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition beta to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.
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