Synlett 2017; 28(13): 1652-1656
DOI: 10.1055/s-0036-1590819
letter
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Cross-Coupling of Ammonia or Primary Alkylamines with (Hetero)aryl Sulfamates, Carbamates, or Pivalates

Preston M. MacQueen
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2, Canada   Email: mark.stradiotto@dal.ca
,
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2, Canada   Email: mark.stradiotto@dal.ca
› Author Affiliations
We are grateful to the Natural Sciences and Engineering Research Council of Canada (Discovery Grant RGPIN-2014-04807 and I2I Grant I2IPJ/485197-2015) and Dalhousie University for their support of this work.
Further Information

Publication History

Received: 16 May 2017

Accepted after revision: 06 June 2017

Publication Date:
14 July 2017 (online)


Abstract

A catalyst system capable of effecting the cross-coupling of ammonia or primary alkylamines with (hetero)aryl sulfamates, carbamates, or pivalates is reported for the first time. The air-stable nickel(II) pre-catalyst C1 tolerates a broad spectrum of heterocyclic functionality within both reaction partners, as well as ether, nitrile, pyrrole, trifluoromethyl, and boronate ester substituents. In the case of reactions involving primary alkylamines and (hetero)aryl sulfamates and carbamates, room-temperature cross-couplings were achieved.

Supporting Information

 
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