Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 4, Pages 1565-1570Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02729
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Funding
- Spanish MINECO/FEDER [CTQ2014-59650-P, CTQ2013-41511-P]
- Principality of Asturias (Spain) [GRUPIN14-013]
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The mechanisms of the reaction between non-heteroatom-stabilized alkynyl chromium carbene complexes prepared in situ and furfural imines to yield benzofurans and/or azetines have been explored by means of density functional theory method calculations. The reaction proceeds through a complex cascade of steps triggered by a nucleophilic addition of the imine nitrogen atom. The formation of two benzofuran regioisomers has been explained in terms of competitive nucleophilic attacks to different positions of the carbene complex. Each of these regioisomers can be obtained as the major product depending on the starting materials. The overall sequence could be controlled to yield benzofurans or azetines by adjusting the substituents present in the initial carbene complex. This mechanistic information allowed for the preparation of new benzofurans and azetinylcarbenes in good yields.
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