ACS Combinatorial Science
Letter
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reactions to be run with minimal additional optimization
necessary. Ultimately, an operationally simple and high yielding
allene synthesis was established that displays a significantly
broadened substrate scope in comparison to the originally
devised traceless Petasis coupling,3 as it obviates the presence of
a hydroxyl activating group. The results of the study delineated
herein also set the stage for the further development and
refinement of SAMDI mass spectrometry-based methods for
future application to other organic reactions.
ASSOCIATED CONTENT
■
S
* Supporting Information
The Supporting Information is available free of charge on the
Complete details of the high-throughput SAMDI mass
spectrometry setup, all experimental procedures, and
complete characterization for all new compounds (IR,
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(16) Kolodych, S.; Rasolofonjatovo, E.; Chaumontet, M.; Nevers, M.-
AUTHOR INFORMATION
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Corresponding Authors
́
C.; Creminon, C.; Taran, F. Discovery of Chemoselective and
Biocompatible Reactions Using a High-Throughput Immunoassay
Screening. Angew. Chem., Int. Ed. 2013, 52, 12056−12060.
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S. A. Label-Assisted Mass Spectrometry for the Acceleration of
Reaction Discovery and Optimization. Nat. Chem. 2013, 5, 423−427.
(18) Cypes, S.; Hagemeyer, A.; Hogan, Z.; Lesik, A.; Streukens, G.;
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Screening of Low Temperature Co Oxidation Catalysts Using Ir
Thermography. Comb. Chem. High Throughput Screening 2007, 10,
25−35.
Author Contributions
The manuscript was written through contributions of all
authors. All authors have given approval to the final version of
the manuscript. A.B.D. and S.L. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(19) Preshlock, S. M.; Ghaffari, B.; Maligres, P. E.; Krska, S. W.;
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M. T.; Chirik, P. J. Cobalt Precursors for High-Throughput Discovery
of Base Metal Asymmetric Alkene Hydrogenation Catalysts. Science
2013, 342, 1076−1080.
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Tosylhydrazones with Terminal Alkynes Catalyzed by Copper(I):
Synthesis of Trisubstituted Allenes. Angew. Chem., Int. Ed. 2011, 50,
1114−1117.
(23) Tang, X.; Zhu, C.; Cao, T.; Kuang, J.; Lin, W.; Ni, S.; Zhang, J.;
Ma, S. Cadmium Iodide-Mediated Allenylation of Terminal Alkynes
with Ketones. Nat. Commun. 2013, 4, 2450.
We gratefully acknowledge financial support from Northwest-
ern University, and the National Science Foundation
(CHE1361173 to R.J.T.). A.B.D. thanks the ARCS Foundation
for the Daniel F. and Ada L. Rice Foundation Scholarship.
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