期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 70, 页码 16022-16031出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904156
关键词
alkenylation; C-H activation; cyclopentadienyl ligands; Lossen rearrangement; rhodium
资金
- JSPS (Japan) [17K14481]
- JSPS [18J13654]
- Umicore
- Grants-in-Aid for Scientific Research [18J13654, 17K14481] Funding Source: KAKEN
It has been established that a cyclopentadienyl (Cp) Rh-III complex with two aryl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/alkenylation cascade of N-pivaloyl heterole carboxamides with internal alkynes, leading to alkenylheteroles. Interestingly, the use of sterically demanding internal alkynes afforded not the alkenylation but the [3+2] annulation products ([5,5]-fused heteroles). In these reactions, the pendant amide moiety of the CpRhIII complex may accelerate the formal Lossen rearrangement. The use of five-membered heteroles may deter reductive elimination to form strained [5,5]-fused heteroles; instead, protonation proceeds to give the alkenylation products. Bulky alkyne substituents accelerate the reductive elimination to allow the formation of the [5,5]-fused heteroles.
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