Synlett 2017; 28(11): 1321-1326
DOI: 10.1055/s-0036-1588760
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Highly Efficient Esterification of Aldehydes with N-Hydroxyphthalimide via Cross-Dehydrogenative Coupling in Water at Room Temperature

Zhicheng Guo
a  Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Xinpeng Jiang
b  College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Can Jin*
b  College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Jiadi Zhou
a  Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Bin Sun
a  Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Weike Su*
a  Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 18 January 2017

Accepted after revision: 27 February 2017

Publication Date:
27 March 2017 (online)


Abstract

A copper-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide and aldehydes using PhI(OAc)2 as an oxidant is described. It is reported for the first time to synthesize NHPI esters in water, providing the corresponding NHPI esters in moderate to good yields. This facile and efficient method is eco-friendly and possesses the advantages of mild conditions, short reaction time, and broad substrate scope.

Supporting Information

 
  • References and Notes

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  • 18 General Experimental Procedure to Synthesize 1,3-Dioxoisoindolin-2-yl 2-fluorobenzoate (3b) A flame-dried flask was charged with Cu (10 mol%) and Selectfluor (10 mol%) in H2O (8 mL) was added and stirred at r.t. for 5 min, then 2-fluorobenzaldehyde (1, 1.2 mmol), NHPI (2, 1 mmol), PhI(OAc)2 (1.2 mmol) were added, the resulting mixture was whisked for a further 15 min in water at r.t. After the reaction was finished (monitored by TLC), CH2Cl2 (10 mL) was added, then the organic layer was separated and dried over Na2SO4. The solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel (n-hexane–EtOAc, 10:1) to afford the corresponding product 3b in 75% yield (214 mg) as white solid; mp 170–172 °C. 1H NMR (500 MHz, CDCl3): δ = 8.16–8.13 (m, 1 H), 7.95–7.91 (m, 2 H), 7.84–7.81 (m, 2 H), 7.12–7.67 (m, 1 H), 7.33–7.31 (m, 1 H), 7.28–7.24 (m, 1 H). 13C NMR (126 MHz, CDCl3): δ = 162.5 (1 J C–F = 264.6 Hz), 161.9, 160.2 (4 J C–F = 5.0 Hz), 136.7 (3 J C–F = 10.1 Hz), 134.9, 132.7, 128.9, 124.4 (4 J C–F = 3.8 Hz), 124.0, 117.4 (2 J C–F = 21.4 Hz), 113.9 (3 J C–F = 10.0 Hz).