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Issue 29, 2011
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Pd–carbene catalyzed carbonylation reactions of aryl iodides

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Abstract

A series of carbene complexes [PdBr2(iPr2-bimy)L] (C2–C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd–NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(II)–NHC complex in different types of carbonylations of aryl iodides under mild conditions.

Graphical abstract: Pd–carbene catalyzed carbonylation reactions of aryl iodides

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Publication details

The article was received on 15 Mar 2011, accepted on 28 Apr 2011 and first published on 15 Jun 2011


Article type: Paper
DOI: 10.1039/C1DT10433K
Dalton Trans., 2011,40, 7632-7638

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    Pd–carbene catalyzed carbonylation reactions of aryl iodides

    L. Xue, L. Shi, Y. Han, C. Xia, H. V. Huynh and F. Li, Dalton Trans., 2011, 40, 7632
    DOI: 10.1039/C1DT10433K

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