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Synlett 2011(5): 643-646  
DOI: 10.1055/s-0030-1259556
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Isoindole Derivatives by Palladium-Catalyzed Domino Reaction of (2-Alkynyl)phenylketone O-Pentafluorobenzoyloximes

Mitsuru Kitamura*, Yohei Moriyasu, Tatsuo Okauchi
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu 804-8550, Japan
e-Mail: +81(93)8843304; e-Mail: kita@che.kyutech.ac.jp;
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Publication History

Received 12 January 2011
Publication Date:
11 February 2011 (online)

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Abstract

Isoindole derivatives were synthesized by the palladium-catalyzed cyclization of (2-alkynyl)phenylketone O-pentafluoro­benzoyloximes in the presence of organometallic compounds such as sodium formate and aryl boronic acid.

Key words

domino reaction - isoindoles - Mizoroki-Heck reaction - oximes - palladium

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13

Oxime 7a was synthesized from 2-hydroxybenzophenone in 4 steps: i) (CF3SO2)2O, N,N-dimethyl-4-aminopyridine (cat.), pyridine, CH2Cl2, -78 ˚C to 0 ˚C, 1.5 h (99% yield); ii) PhCºCH, Pd(PPh3)4 (cat.), CuI (cat.), Et3N, n-Bu4NBr, DMF, 70 ˚C, 2.5 h (97% yield);¹4 iii) NH2OH˙HCl, pyridine, 100 ˚C, 2.5 h (86% yield); iv) C6F5COCl, Et3N, CH2Cl2,
0 ˚C, 0.5 h (92% yield). Other (2-alkynyl)phenylketone
O-pentafluorobenzoyloximes were synthesized in a similar way of the synthesis of 7a.