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Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium‐Catalyzed Enantioselective C(sp3)–H Functionalization
Open accessAbstract
Teaming up: The important indoline scaffold is provided with enantiomeric ratios of up to 98:2 in palladium(0)-catalyzed C(sp3)–H activations of aryl triflates. The key is the combination of the electron-rich monodentate Sagephos and the bulky 9H-xanthene-9-carboxylic acid. Both participate in a highly cooperative manner in the enantiodetermining concerted-deprotonation-metalation step (see scheme, Tf=triflate).
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Citations
Cited by
Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)–H Bonds
Liu, B., Romine, A. M., Rubel, C. Z., Engle, K. M., & Shi, B.-F. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00519 · Cited by 538
Engle, K. M., & Yu, J.-Q. (2013) · The Journal of Organic Chemistry · doi:10.1021/jo400159y · Cited by 531
Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides
Jain, P., Verma, P., Xia, G., & Yu, J.-Q. (2017) · Nature Chemistry · doi:10.1038/nchem.2619 · Cited by 336
Metadata
- Authors
- Saget, T., Lemouzy, S. J., & Cramer, N.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2012-02-03
- Volume
- 51
- Issue
- 9
- Pages
- 2238-2242
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2167167027
- Cited by
- 263
- References
- 0
- FWCI
- 13.85
- Type
- journal article
- Language
- en
- Open access
- green
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- Saget, T., Lemouzy, S. J., & Cramer, N. (2012). Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium‐Catalyzed Enantioselective C(sp3)–H Functionalization. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201108511
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