Organometallics
Communication
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Scheme 3. Scope of Selective Monoarylation of Ortho-
Substituted Aryl Halides with Ammonia using 6 and 10
a
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a
1
Yields of isolated material, X = Cl, mono:di ratio determined by H
NMR spectroscopy of the crude reaction mixture. Reactions with 6
were run with 2 mol % catalyst, whereas reactions with 10 used 1 mol
b
1
% catalyst. Product yield determined by H NMR spectroscopy with
1,4-bis(trichloromethyl)benzene internal standard. X = Br. A 2 mol
% portion of 10 was used.
c
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̈
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
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̈
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General experimental details, details of compound
synthesis, and characterization data (PDF)
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(30) See Table S1 in the Supporting Information.
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(33) (a) Pd-PEPPSI-IHept was first prepared in 2008 and disclosed
at the 238th American Chemical Society National Meeting, August 16,
2009: “The Role of Bulkiness in Promoting Pd-NHC-Catalysed Cross-
Couplings: A Synergy Between Experiment, Spectroscopy, and
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(36) Potassium carbonate and potassium phosphate gave no
conversion to product.
AUTHOR INFORMATION
Corresponding Author
ORCID
Notes
The authors declare the following competing financial
interest(s): Some of the catalysts in this manuscript are
commercially available and the Principal author receives
royalies from their sales.
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ACKNOWLEDGMENTS
■
This work was supported by the NSERC of Canada in the form
of a CRD grant and by the Eli Lilly Research Award Program
(LRAP).
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