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Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination

✍ Scribed by Robert A. Singer; Stephen L. Buchwald


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
280 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


Palladium-catalyzed amination reactions were carried out with 2-triflato-2'-(4methoxybenzyloxy)-1,1'-binaphthyl (5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2'-hydroxy-1,1'binaphthyl (1). Arylamines were also coupled successfully with 5 under similar conditions.


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A practical synthesis of 2-amino-2%-hydroxy-1,1%-binaphthyl (NOBIN) was realized from BINOL through a single step. Its facile purification procedure makes the process amenable for large scale synthesis of NOBIN.