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Access to Benzazepinones by Pd-Catalyzed Remote C-H Carbonylation of γ-Arylpropylamine Derivatives

Author
Martínez-Mingo, Mario; Rodríguez, Nuria; Gómez Arrayás, Ramón; Carretero, Juan C.
Entity
UAM. Departamento de Química Orgánica
Publisher
American Chemical Society
Date
2019-06-07
Citation
Organic Letters 21.11 (2019): 4345-4349
ISSN
1523-7052 (online); 1523-7060 (print)
DOI
10.1021/acs.orglett.9b01523
Funded by
We thank the Spanish Ministerio de Economía y Competitividad (Project CTQ2015-66954-P, MINECO/FEDER, UE) for financial support. M.M.-M. thanks MINECO for a FPI predoctoral fellow-ship. N.R. thanks the European Commission for a Marie Curie Ca-reer Integration Grant (CIG: CHAAS-304085). Prof. Inés Alonso (Departamento de Química Orgánica, UAM) is gratefully acknowl-edged for helpful discussions
Project
Gobierno de España. CTQ2015-66954-P; info:eu-repo/grantAgreement/EC/FP7/304085
Editor's Version
https://doi.org/10.1021/acs.orglett.9b01523
Subjects
Activation analysis; Catalysis; Bond functionalization; Química
URI
http://hdl.handle.net/10486/688514
Note
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b01523. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b01523. Experimental procedures and spectral data for all new compounds (PDF): https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.9b01523/suppl_file/ol9b01523_si_001.pdf
Rights
© 2019 American Chemical Society

Abstract

A general method for the construction of seven-membered rings through Pd-catalyzed C(sp2)-H carbonylation at the remote ϵ-position of γ-arylpropylamine derivatives, including chiral α-amino acids, has been developed using Mo(CO)6 as the CO source, furnishing richly functionalized benzo[c]azepin-1-one derivatives. The readily removable N-SO2Py protecting/directing group provides high levels of chemo-, regio- and diastereoselectivity. Furthermore, this method is amenable to the postsynthetic modification of complex molecules such as small peptides
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