期刊
SYNTHESIS-STUTTGART
卷 53, 期 17, 页码 3001-3010出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1502-3641
关键词
furans; pyrroles; indoles; alkynes; palladium; oxygen; benzannulation
资金
- National Research Foundation of Korea [NRF-2019R1A2C1007852, NRF-2019R1A4A1028007]
- Ministry of Science and Technology of Taiwan [MOST108-2113M009-020-MY3]
A benzannulation strategy was developed involving activation of two C-H bonds of five-membered heteroarenes, resulting in fluorescent benzofuran and indole derivatives through Pd-catalyzed oxidative reactions. This strategy provides a potential pathway for further development of functionalized polycyclic heteroaromatic compounds.
A benzannulation strategy involving activation of two C-H bonds of five-membered heteroarenes was developed. Readily available furans and pyrroles stabilized by synthetically useful electron-withdrawing groups underwent Pd-catalyzed 1:2 annulation reactions with diaryl alkynes. A variety of functional groups, including ester, amide, ketone, aldehyde, and nitrile, on the heterocyclic cores were tolerated in the Pdcatalyzed oxidative reactions. In these reactions, the combination of 2,2-dimethylbutyric add and its conjugate base facilitated metalation at the heteroaromatic rings and reoxidation of the Pd(0) species using oxygen as the terminal oxidant. This strategy provides fluorescent benzofuran and indole derivatives and is expected to allow for further development of functionalized polycyclic heteroaromatic compounds.
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