Synthesis 2021; 53(22): 4290-4296 DOI: 10.1055/s-0040-1719842
special topic
Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award
Dearomative syn -1,2-Diamination of Benzene and Naphthalene
Christopher W. Davis
,
Tanner W. Bingham
,
Mikiko Okumura
,
Financial support for this work was provided by the University of Illinois at Urbana-Champaign and the NIH/National Institute of General Medical Sciences (R01GM122891). Amgen, Eli Lilly and Company, FMC Corporation, and Bristol-Myers Squibb are also acknowledged for unrestricted research support.
Dedicated to Prof. Sarah Reisman on occasion of winning the 2019 Dr. Margaret Faul Women in Chemistry Award
Abstract
We report the palladium-catalyzed, dearomative syn -1,2-diamination of the non-activated arenes benzene and naphthalene using aryl isocyanates. This reaction proceeds with exclusive syn -1,2-selectivity and provides a complementary regio- and stereoselectivity to previously described arenophile-based transformations. The products are amenable to further synthetic elaboration, including selective diene functionalization and heterocycle cleavage. Overall, this dearomatization provides synthetic access to unprecedented saturated nitrogen-containing heterocyclic motifs and syn -1,2-diaminated cyclohexane products.
Key words
dearomatization -
amine -
heterocycle -
palladium -
catalysis -
isocyanate
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719842.
Supporting Information
Publication History
Received: 03 September 2021
Accepted: 22 September 2021
Article published online: 29 September 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany
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