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Synfacts 2005(1): 0159-0159  
DOI: 10.1055/s-2005-872138
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Directed Metalation and Cross-Coupling of N,N-Dialkyl Aryl O-Sulfamates

Contributor(s): Paul Knochel, Andrei Gavryushin
T. K. Macklin, V. Snieckus*
Queen’s University, Kingston, Canada
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Publikationsdatum:
21. September 2005 (online)

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Significance

N,N-Dialkyl sulfamate can serve as an ortho-directing group in the metalation reaction as well as a leaving group in Ni-catalyzed cross-coupling. Such properties lead to a powerful synthetic strategy for the preparation of polyfunctionalized arenes and hetarenes, starting from aryl O-sulfamates.