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Synthesis of Substituted Dihydrobenzofurans via Tandem S_NAr/5-Exo-Trig Cyclization

Koy, Maximilian and Engle, Keary M. and Henling, Lawrence M. and Takase, Michael K. and Grubbs, Robert H. (2015) Synthesis of Substituted Dihydrobenzofurans via Tandem S_NAr/5-Exo-Trig Cyclization. Organic Letters, 17 (8). pp. 1986-1989. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20150413-091100878

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Abstract

A tandem S_NAr/5-exo-trig cyclization reaction is reported that converts N-alkyl- and -arylimines derived from o-fluorobenzaldehydes into 3-amino-2,3-dihydro-2,2-diarylbenzofurans in moderate to good yields. Diarylmethoxide coupling partners serve the dual role of nucleophile in the S_NAr step and catalytic base in the cyclization step. With a subset of the substrates, a further base-induced elimination of the 3-amino-2,3-dihydro-2,2-diarylbenzofuran to a phenolic enamine was observed.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.5b00743DOIArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b00743PublisherSupporting Information
ORCID:
AuthorORCID
Engle, Keary M.0000-0003-2767-6556
Takase, Michael K.0000-0001-8365-3645
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2015 American Chemical Society. Received: March 13, 2015. Publication Date (Web): April 8, 2015. The research described in this paper was supported financially by the ONR (Award No. N00014-12-1-0596), the DAAD (RISE Worldwide Fellowship to M.K.), and the NIH NIGMS (Award No. F32GM108145; postdoctoral fellowship to K.M.E.). Zachary K. Wickens (Grubbs laboratory, Caltech), Dr. Hans Renata (Arnold laboratory, Caltech), and Dr. Will R. Gutekunst (Hawker laboratory, UCSB) are acknowledged for helpful discussions. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology (CHE-0639094).
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)N00014-12-1-0596
Deutscher Akademischer Austauschdienst (DAAD)UNSPECIFIED
NIH Postdoctoral FellowshipF32GM108145
NSFCHE-0639094
Issue or Number:8
Record Number:CaltechAUTHORS:20150413-091100878
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150413-091100878
Official Citation:Synthesis of Substituted Dihydrobenzofurans via Tandem SNAr/5-Exo-Trig Cyclization Maximilian Koy, Keary M. Engle, Lawrence M. Henling, Michael K. Takase, and Robert H. Grubbs Organic Letters 2015 17 (8), 1986-1989 DOI: 10.1021/acs.orglett.5b00743
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:56587
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Apr 2015 16:25
Last Modified:06 May 2020 22:13

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