Direct access to anthranilic acid derivatives via CO2 incorporation reaction using arynes

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3845-3847

  Yoshida, Hiroto ^a   Morishita, Takami ^a   Ohshita, Joji ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349134773     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801588s     Document Type: Article

References (30)

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7. Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040.
8. Other three-component coupling reactions of arynes which proceed through a zwitterionic intermediate have been reported: (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed 2004, 43, 3935.
9. (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659.
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22. We have already reported on synthesis of 2-aminobenzhydrols (or 2-aminobenzhydrylamines) based on three-component coupling reactions of arynes, aminosilanes, and aldehydes (or sulfonylimines). In these reactions, the use of amines as nucleophiles in lieu of aminosilanes led to considerable lowering of the product yields in contrast to the results described herein. (a) Yoshida, H.; Morishita, T.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2007, 9, 3367.
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27. In the reactions with low yields of 3, an aniline derivative and some unidentified compounds were formed as side products.
28. The reason for the longer reaction time (for example, entries 6, 11, and 12) is due to slow consumption of benzyne precursor 1a.
29. A similar regioselectivity, which can be attributed to the strong electron-withdrawing effect of a fluorine atom, was observed in other three-component couplings with 4-fluorobenzyne. See refs 3, 4, and 7.
30. Preliminary experiments revealed that primary amines and aminosilanes also gave the respective three-component coupling products, which will be reported in due course.