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Synthesis of 2,4,5-Trisubstituted Furans via a Triple C(sp3)–H Functionalization Reaction Using Rongalite as the C1 Unit

Author:
Wang, Miao, Xiang, Jia-Chen, Cheng, Yan, Wu, Yan-Dong, Wu, An-Xin
Source:
Organic letters 2016 v.18 no.3 pp. 524-527
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, formaldehyde, furans, iodine, ketones, nitrates
Abstract:
A highly efficient I₂/Cu(NO₃)₂·3H₂O-mediated triple C(sp³)–H functionalization reaction for the synthesis of 2,4,5-trisubstituted furans from aryl methyl ketones and rongalite by employing rongalite as a C1 unit has been developed. This method allows rapid access to (2-acyl-4-methylthio-5-aryl) furans. Preliminary mechanistic studies indicate that in situ generated dimethyl(phenacyl)-sulfonium iodine and HCHO were probably the key intermediates in this transformation.
Agid:
5792303