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Synfacts 2007(2): 0136-0136  
DOI: 10.1055/s-2006-955826
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Hydroaminative Route to Phosphaisoquinolin-1-ones

Contributor(s): Victor Snieckus, Bärbel Wittel
W. Tang, Y.-X. Ding*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

A Pd-catalyzed intramolecular cyclization of o-(1-alkynyl)phenylphosphoramide esters to give phosphaisoquinolin-1-ones is reported. This formally 6-endo-dig hydroaminative reaction proceeds in good yields and high regio­selectivities. The o-(1-alkynyl)phenylphosphor­amide esters are prepared by a two-step process involving treatment of o-(1-alkynyl)phenylphosphoric acid esters with thionyl chloride followed by amination of the resulting phosphonyl chloride with amines (R. Hirschmann et al. J. Am. Chem. Soc. 1997, 119, 8177-8190). Although different Pd, Ag, and Cu catalysts were tested, PdCl2(MeCN)2 was shown to afford by far the best yields in shorter reaction times. The scope of the reaction was inadequately studied.