Exploitation of differential reactivity of the carbon–chlorine bonds in 1, 3-dichloroisoquinoline. Routes to new N, N-chelate ligands and 1, 3-disubstituted isoquinolines

A Ford, E Sinn, S Woodward

Index: Ford, Alan; Sinn, Ekkehard; Woodward, Simon Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 927 - 934

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Citation Number: 41

Abstract

Under Pd (PPh3) 4 catalysis, coupling of arylboronic acids to the 1-position of 1, 3- dichloroisoquinoline takes place, leading exclusively to 1-aryl-3-chloroisoquinolines. This regiochemistry is demonstrated by the crystal structure of 3-chloro-1-(8-methoxy-1-naphthyl) isoquinoline. The 3-chloro group may be modified by nickel-catalysed reaction with Grignard reagents or direct nucleophilic displacement with LiSCH2Ph. Attempted lithiation of the 3- ...