期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 35, 页码 8245-8248出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901518
关键词
annulations; C-H activation; indoles; indolines; rhenium catalysis
资金
- National Natural Science Foundation of China [21772202, 21831008]
- Beijing Municipal Science & Technology Commission [Z181100004218004]
Described herein are rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C-H/C-N bond cleavage, which provide rapid access to fused-ring pyrroloindolone derivatives. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C-H activation reactions, enabled by the unique catalytic trio of Re-2(CO)(10), Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re-2(CO)(10), [MeZnNPh2](2) and Zn(OTf)(2) was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.
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