A practical palladium-catalysed heteroannulation of 2-bromobenzaldehyde with alcohols and carbon monoxide leading to 3-alkoxy-3H-isobenzofuran-1-ones

Journal of Chemical Research - Part S

Volumn , Issue 11, 2002, Pages 550-551

  Cho, Chan Sik ^a   Lim, Dong Kwon ^a   Kim, Tae Jeong ^a   Shim, Sang Chul ^a  

^a Kyungpook National University   (South Korea)

Author keywords

2 bromobenzaldehyde; Alcohol; Carbon monoxide; Heteroannulation; Palladium catalyst

Indexed keywords

2 BROMOBENZALDEHYDE; ALCOHOL DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBON MONOXIDE; ISOBENZOFURAN DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0036867052     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823402103170727     Document Type: Article

References (18)

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2. For transition metal-catalysed synthesis of phthalides, see cited refs of ref 10.
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4. M.J. Broadhurst and C.H. Hassall, J. Chem. Soc., Perkin Trans. 1, 1982, 2227; M.A. Bates, P.G. Sammes and G.A. Thomson, J. Chem. Soc., Perkin Trans. 1, 1988, 3037.
5. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
6. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
7. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
8. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
9. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
10. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
11. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
12. For isoindolinones: C.S. Cho, J.W. Lee, D.Y. Lee, S.C. Shim and T.J. Kim, Chem. Commun., 1996, 2115; C.S. Cho, D.Y. Chu, D.Y. Lee, S.C. Shim, T.J. Kim, W.T. Lim and N.H. Heo, Synth. Commun., 1997, 27, 4141; C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1998, 28, 849; C.S. Cho, L. H. Jiang, D.Y. Lee and S. C. Shim, Bull. Korean Chem. Soc., 1996, 17, 1095; C.S. Cho, L.H. Jiang, D.Y. Lee, S. C. Shim, H.S. Lee and S.-D. Cho, J. Heterocycl, Chem., 1997, 34, 1371; C.S. Cho, X. Wu, L.H. Jiang, S. C. Shim, H.-J. Choi and T.J. Kim, J. Heterocycl. Chem. 1998, 35, 265; C.S. Cho, X. Wu, L.H. Jiang, S.C. Shim and H. R. Kim, J. Heterocycl. Chem. 1999, 36, 297; C.S. Cho, H.S. Shim, H.-J. Choi. T.-J. Kim, S.C. Shim and M.C. Kim. Tetrahedron Lett., 2000, 41, 3891.
13. For β-lactams: C.S. Cho, L.H. Jiang and S.C. Shim, Synth. Commun., 1999, 29, 2695.
14. S.C. Shim, D.Y. Lee, L.H. Jiang, T.J. Kim and S.-D. Cho, J. Heterocycl. Chem., 1995, 32, 363.
15. C.S. Cho, D.Y. Baek and S. C. Shim, J. Heterocycl. Chem., 1999, 36, 1101.
16. D.Y. Lee, C.S. Cho, L. H. Jiang, X. Wu and S.C. Shim, Synth. Commun., 1997, 27, 3449.
17. C.S. Cho, D.Y. Baek and S.C. Shim, J. Heterocycl. Chem., 1999, 36, 289.
18. C.S. Cho, D.Y. Baek, H.-Y. Kim, S.C. Shim, D.H. Oh, Synth. Commun., 2000, 30, 1139.