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15.5.1.1.1.2.2.3.1 Variation 1: From N-tert-Butyl-2-iodoarylmethanimines and Alkynes

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515673.

The direct production of isoquinolines by palladium(0)-catalyzed annulation of N-tert-butyl-2-iodoarylmethanimines 53 produces 3,4-disubstituted isoquinolines 55 (Scheme 23).[‌48‌] The mechanism assumed involves initial oxidative palladium insertion into the CI bond, insertion of the arylpalladium thus produced into the alkyne, and then interaction with the imine nitrogen generating a seven-membered palladacycle ammonium salt 54. Collapse to the six-membered ring, with expulsion of palladium(0), and loss of 1-methylpropene from the nitrogen, perhaps encouraged by unfavorable steric interaction between the N-tert-butyl and the 3-substituent, then leads to the product 55.

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