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Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization: Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles
Abstract
A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products.
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Cited by
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Piera, J., & Bäckvall, J. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200700604 · Cited by 889
Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core
Boens, N., Verbelen, B., Ortiz, M. J., Jiao, L., & Dehaen, W. (2019) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2019.213024 · Cited by 396
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Metadata
- Authors
- Beck, E. M., Grimster, N. P., Hatley, R., & Gaunt, M. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-02-02
- Volume
- 128
- Issue
- 8
- Pages
- 2528-2529
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2067408158
- Cited by
- 365
- References
- 0
- FWCI
- 14.56
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization: Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles. https://app.cochat.ai/papers/10.1021/ja058141u
- The paper
- Beck, E. M., Grimster, N. P., Hatley, R., & Gaunt, M. J. (2006). Mild Aerobic Oxidative Palladium (II) Catalyzed C−H Bond Functionalization: Regioselective and Switchable C−H Alkenylation and Annulation of Pyrroles. Journal of the American Chemical Society. https://doi.org/10.1021/ja058141u
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