Lacker, Caitlin R. and DeLano, Travis J. and Chen, Emily P. and Kong, Jongrock and Belyk, Kevin M. and Piou, Tiffany and Reisman, Sarah E. (2022) Enantioselective Synthesis of N-Benzylic Heterocycles by Ni/Photoredox Dual Catalysis. Journal of the American Chemical Society, 144 (44). pp. 20190-20195. ISSN 0002-7863. doi:10.1021/jacs.2c07917. https://resolver.caltech.edu/CaltechAUTHORS:20230125-514893900.20
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Abstract
An asymmetric cross-coupling of α-N-heterocyclic trifluoroborates with aryl bromides using Ni/photoredox dual catalysis has been developed. This C(sp²)–C(sp³) cross-coupling provides access to pharmaceutically relevant chiral N-benzylic heterocycles in good to excellent enantioselectivity when bioxazolines (BiOX) are used as the chiral ligand. High-throughput experimentation significantly streamlined reaction development by identifying BiOX ligands for further investigation and by allowing for rapid optimization of conditions for new trifluoroborate salts.
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| Additional Information: | Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Michael Takase for solving the structure of 5h and the Beckman Institute at Caltech and the Dow Next Generation Instrumentation Grant for support of the small molecule crystallography facility. Fellowship support was provided by the NSF (C.R.L., T.J.D., Grant No. DGE-1144469). S.E.R. acknowledges financial support from the NIH (R35GM118191). This work was supported by Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc., Kenilworth, NJ, USA. We thank Nelo R. Rivera, Wildredo Pinto, and Yongqian Zhang for providing analytical support in obtaining optical rotation, HRMS, and FT-IR characterization data for 5j. We thank Benjamin Sherry, Jamie McCabe Dunn, Louis-Charles Campeau, and Kevin Campos (all employees of Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc., Kenilworth, NJ, USA) for helpful discussions. | ||||||||||||||||
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| Issue or Number: | 44 | ||||||||||||||||
| DOI: | 10.1021/jacs.2c07917 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20230125-514893900.20 | ||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20230125-514893900.20 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 118940 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | Research Services Depository | ||||||||||||||||
| Deposited On: | 22 Feb 2023 19:29 | ||||||||||||||||
| Last Modified: | 22 Feb 2023 19:29 |
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