Palladium-catalyzed coupling of 2-bromoanilines with vinylstannanes. A regiocontrolled synthesis of substituted indoles

…, AF Renaldo, DE Rudisill, JK Stille

Index: Krolski, Michael E.; Renaldo, Alfred F.; Rudisill, Duane E.; Stille, J. K. Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1170 - 1176

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Citation Number: 106

Abstract

'Reactions carried out in refluxing toluene with tosylate of tributylvinylstannane and 2 mol% tetrakis (tripheny1phosphine) pal-ladium for-24 h.* Only starting material was recovered. c2. 25 equiv of tributylvinylstannane gave the bis (etheny1)-N-tosylanilines. of 4-substituted indoles, commercially available 2-amino-3-nitrotoluene (la) and 2-amino-3-nitrophenol (lb) were converted to the corresponding bromides 2 via a Sandmeyer reaction (Scheme I). l2 ...