CaltechAUTHORS
Published April 17, 2015 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology

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.

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).

Attached Files

Supplemental Material - ol5b00743_si_001.pdf

Supplemental Material - ol5b00743_si_002.cif

Supplemental Material - ol5b00743_si_003.cif

Supplemental Material - ol5b00743_si_004.cif

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Additional details

Identifiers

Eprint ID
56587
DOI
10.1021/acs.orglett.5b00743
Resolver ID
CaltechAUTHORS:20150413-091100878

Related works

Describes
10.1021/acs.orglett.5b00743 (DOI)

Funding

Office of Naval Research (ONR)
N00014-12-1-0596
Deutscher Akademischer Austauschdienst (DAAD)
NIH Postdoctoral Fellowship
F32GM108145
NSF
CHE-0639094

Dates

Created
2015-04-13
Created from EPrint's datestamp field
Updated
2021-11-10
Created from EPrint's last_modified field