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

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

References and Notes

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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.