期刊
ACS CATALYSIS
卷 4, 期 1, 页码 195-202出版社
AMER CHEMICAL SOC
DOI: 10.1021/cs400661q
关键词
carbamate; carbonylation; DBU; diphenyl carbonate; N-heteroaromatics; organic carbonate; organocatalysis; phosgene substitution
资金
- Universita degli Studi Aldo Moro, Bari (Fondi di Ateneo)
Polymer-bound DBU (PS-DBU, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) is an effective and selective catalyst for solventless N-phenoxycarbonylation of N-heteroaromatics (pyrrole (1), indole (2), and carbazole (3)) with diphenyl carbonate (DPC), used as an eco-friendly active carbonyl species in place of phosgene-derivatives. The immobilized catalyst is less active than unsupported DBU but can be recovered easily at the end of catalytic run and recycled effectively. Dedicated studies have demonstrated that DBLJ can react as a nucleophile with DPC even when it is anchored on the polymeric matrix, and provided the first direct evidence (FTIR and solid-state C-13 NMR) of formation of a 8-carboxy-substituted 1,8-diazabicyclo[5.4.0]undec-7-enium cation in DBLJ-promoted nucleophilic activation of carbonic acid diesters.
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