Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations

Burns, David J.; Lam, Hon Wai

Abstract

1,3?Enynes containing allylic hydrogens cis to the alkyne are shown to act as one?carbon partners, rather than two?carbon partners, in various rhodium?catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C--H activation, involving a hitherto rare example of the 1,4?migration of a RhIII species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.

Citation

Burns, D. J., & Lam, H. W. (2014). Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations. Angewandte Chemie International Edition, 53(37), https://doi.org/10.1002/anie.201406072

• Journal Article Type: Article
• Acceptance Date: Jun 30, 2014
• Publication Date: Sep 8, 2014
• Deposit Date: Aug 18, 2018
• Publicly Available Date: Sep 24, 2018
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 53
• Issue: 37
• DOI: https://doi.org/10.1002/anie.201406072
• Public URL: https://nottingham-repository.worktribe.com/output/1100624
• Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201406072
• PMID: 00034267