One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration

Dooley, Johnathon D.; Lam, Hon Wai

Abstract

Rhodium(III)-catalyzed C-H functionalization-oxidative annulations of aromatic substrates with 1,3-enynes that contain allylic hydrogen atoms cis to the alkyne are described. The key step in these reactions is an alkenyl-to-allyl 1,4-rhodium(III) migration to give electrophilic pi-allylrhodium(III) species. Nucleophilic trapping of these species gives heterocycles such as benzopyrans, isobenzofuranones, and isoindolinones.

Citation

Dooley, J. D., & Lam, H. W. (2018). One-carbon oxidative annulations of 1,3-enynes by catalytic C–H functionalization and 1,4-rhodium(III) migration. Chemistry - A European Journal, 24(16), 4050-4054. https://doi.org/10.1002/chem.201706043

• Journal Article Type: Article
• Acceptance Date: Jan 22, 2018
• Online Publication Date: Jan 22, 2018
• Publication Date: Mar 15, 2018
• Deposit Date: Jan 24, 2018
• Publicly Available Date: Jan 23, 2019
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 16
• Pages: 4050-4054
• DOI: https://doi.org/10.1002/chem.201706043
• Keywords: catalysis; C-H functionalization; enyne; Isomerization; rhodium
• Public URL: https://nottingham-repository.worktribe.com/output/920314
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201706043/full
• Additional Information: This is the pre-peer reviewed version of the following article: Dooley, J. D. and Lam, H. W. (), One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration. Chem. Eur. J.. Accepted Author Manuscript, which has been published in final form at http://dx.doi.org/10.1002/chem.201706043. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
• Contract Date: Jan 24, 2018