Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones via the Simultaneous α-Iodination and N^β-Arylation by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)₂

Abstract

During the studies on the intramolecular cyclization of 4-arylamino-2(5H)-furanones via the Pd-catalyzed C-H activation, a kind of difunctionalization reaction caused by the designed oxidant PhI(OAc)₂ [(diacetoxyiodo)benzene, DIB] was accidentally discovered. When 1.5 eq. DIB is used as a difunctionalizable transfer reagent in the 40 h reaction at 60°C and CH₃CN as solvent, 4-diarylamino-3-iodo-2(5H)-furanones can be obtained with the yields of 57–91% (usually more than 73%). The simultaneous α-iodination and N ^β -arylation reaction without metal catalyst is efficient and convenient. This novel utilization with a greater atom economy provides a simple and practical conversion route for the synthesis of the potential biological 2(5H)-furanone compounds containing multifunctional groups.

GRAPHICAL ABSTRACT

Keywords:

• (Diacetoxyiodo)benzene
• difunctionalization
• iodination
• 2(5H)-furanone
• N-arylation

Notes

^a Reaction conditions: 5-methoxy-4-phenylamino-2(5H)-furanone 1a (0.2 mmol) and solvent (totally 10 mL).

^b Isolated yield.

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