Iron-catalyzed indolizine synthesis from pyridines, diazo compounds, and alkynes

Douglas, Tim; Pordea, Anca; Dowden, James

Abstract

The iron (III) catalyzed synthesis of indolizines from commercially available alkyne, pyridine, and diazo precursors is reported. This mild, expedient method is tolerant of various solvents and proceeds with as little as 0.25 mol % [Fe(TPP)Cl]. Significantly, this multicomponent reaction is compatible with electrophilic alkynes; control experiments demonstrate the importance of the catalyst in promoting pyridinium ylide formation over background reactivity.

Citation

Douglas, T., Pordea, A., & Dowden, J. (in press). Iron-catalyzed indolizine synthesis from pyridines, diazo compounds, and alkynes. Organic Letters, 19(23), https://doi.org/10.1021/acs.orglett.7b03252

• Journal Article Type: Article
• Acceptance Date: Nov 15, 2017
• Online Publication Date: Nov 16, 2017
• Deposit Date: Nov 20, 2017
• Publicly Available Date: Nov 17, 2018
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 23
• DOI: https://doi.org/10.1021/acs.orglett.7b03252
• Public URL: https://nottingham-repository.worktribe.com/output/895207
• Publisher URL: http://pubs.acs.org/doi/10.1021/acs.orglett.7b03252
• Contract Date: Nov 20, 2017