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High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides
Becica, Joseph Hruszkewycz, Damian Steves, Janelle Elward, Jennifer Leitch, David
Becica, Joseph
Hruszkewycz, Damian
Steves, Janelle
Elward, Jennifer
Leitch, David
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Pre-print
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2019-06-09
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Chemistry
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https://doi.org/10.26434/chemrxiv.9108461.v2
Abstract
Sulfonamides are poor nucleophiles in Pd C-N coupling catalysis, hindering synthesis of densely-functionalized N,N-diaryl sulfonamide motifs relevant to medicinal chemistry. Through targeted high-throughput experimentation (HTE), we have identified the Pd/AdBippyPhos catalyst system as an effective and general method to construct this difficult to access moiety. In particular, AdBippyPhos is critical for the installation of heteroaromatic groups. Computational steric parameterization of the investigated ligands reveals the potential importance of remote steric demand, where a large cone angle combined with an accessible Pd center is correlated to successful catalysts for C-N coupling reactions.
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Becica, Joseph; Hruszkewycz, Damian; Steves, Janelle; Elward, Jennifer; Leitch, David; Dobereiner, Graham (2019): High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides. ChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.9108461.v2
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