A telescoped Knochel-Hauser/Kumada-Corriu coupling strategy to functionalized aromatic heterocycles |
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| Authors: | Kyle Clagg Sara Hold Archana Kumar Stefan G. Koenig Remy Angelaud |
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| Affiliation: | 1. Small Molecule Process Chemistry, Genentech, Inc, 1 DNA Way, South San Francisco, CA 94080, USA;2. Small Molecule Analytical Chemistry and Quality Control, Genentech, Inc, 1 DNA Way, South San Francisco, CA 94080, USA |
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| Abstract: | The direct application of Knochel-Hauser derivative arylmagnesium halides in Kumada-Corriu couplings is described. By utilizing the in situ-generated Grignard reagents, the transmetalation with stoichiometric zinc salts to known Negishi coupling conditions is avoided, thereby streamlining the transformation. Several aromatic hetereocycles participate in the deprotonation and couple with a variety of phenyl iodides and bromides in isolated yields up to 81%. The parent system is demonstrated on 6?g scale with 79% yield, and monitored via ReactIR to show the stability of the Grignard and progression of the deprotonation/C | |
| Keywords: | Kumada-Corriu cross-coupling Knochel-Hauser base Sustainability ReactIR |
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