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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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Supplementary files

Article information


Submitted
15 Mar 2011
Accepted
28 Apr 2011
First published
15 Jun 2011

Dalton Trans., 2011,40, 7632-7638
Article type
Paper

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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