Metal-Free Solvent/Base-Switchable Divergent Synthesis of Multisubstituted Dihydrofurans
Babasaheb Sopan Gore1, Chiao-Ying Kuo1, Amol Milind Garkhedkar1
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shiquan First Road, Sanmin District, Kaohsiung City, 807, Taiwan.
Abstract:
A general protocol for the synthesis of multisubstituted 2,3-dihydrofuran-2-carbonitriles and 4,5-dihydrofuran-3-carbonitriles was demonstrated under a metal-free regime with the same oxidant, TBHP. By simply switching the reaction solvent and base, the reaction proceeds via two pathways. An unexpected -CN group migration rearrangement and hydroxylation have occurred in nonpolar and polar solvents, respectively, under the reported conditions. Furthermore, the source of the hydroxyl group and hydrogen in the reaction is indirectly confirmed with isotope labeling studies.
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