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Synlett 2018; 29(14): 1881-1886
DOI: 10.1055/s-0037-1609911
letter
© Georg Thieme Verlag Stuttgart · New York

Photoredox-Catalyzed Decarboxylative C–H Acylation of Heteroarenes

Wei Jia
State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518005, P. R. of China   Email: xyyang@hit.edu.cn   Email: xiawj@hit.edu.cn
,
Yong Jian
State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518005, P. R. of China   Email: xyyang@hit.edu.cn   Email: xiawj@hit.edu.cn
,
Binbin Huang
State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518005, P. R. of China   Email: xyyang@hit.edu.cn   Email: xiawj@hit.edu.cn
,
Chao Yang*
State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518005, P. R. of China   Email: xyyang@hit.edu.cn   Email: xiawj@hit.edu.cn
,
Wujiong Xia  *
State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518005, P. R. of China   Email: xyyang@hit.edu.cn   Email: xiawj@hit.edu.cn
› Author AffiliationsWe are grateful for the financial supports from China NSFC (Nos. 21372055, 21472030 and 21672047), SKLUWRE (No. 2018DX02)
Further Information

Publication History

Received: 15 June 2018

Accepted after revision: 24 June 2018

Publication Date:
23 July 2018 (online)

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Abstract

A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly realize the acylation of various heterocyclic compounds.

Key words

2,2-diethoxyacetic acid - α-keto acids - heterocycles - C–H functionalization - acylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609911.
  • Supporting Information
 

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  • 18 Procedure A for Compounds 3a–pHeterocycle (0.10 mmol), ammonium persulfate (0.30 mmol) and Cs2CO3 (0.20 mmol) were placed in a dry glass tube. Anhydrous DMSO (1 mL) and 2,2-diethoxyacetic acid (0.7 mmol) were injected into the tube by syringe under N2 atmosphere. The solution was then stirred at room temperature under the irradiation of 15 W blue LEDs strip for 24 h. After completion of the reaction, the mixture was quenched by addition of 1.2 mL of 3.0 M HCl and stirred for another 20 h. Then saturated Na2CO3 solution was added to adjust pH to basic. The system was extracted with CH2Cl2, the combined organic layers were washed with brine, then dried over anhydrous Na2SO4. The desired products were obtained in the corresponding yields after purification by flash chromatography on silica gel eluting with PE and EtOAc.Isoquinoline-1-carbaldehyde (3a)Yellow oil. 1H NMR (400 MHz, CDCl3): δ = 10.38 (s, 1 H), 9.38–9.22 (m, 1 H), 8.74 (d, J = 5.5 Hz, 1 H), 7.97–7.82 (m, 2 H), 7.83–7.68 (m, 2 H). 13C NMR (151 MHz, CDCl3): δ = 195.79, 195.74, 149.88, 142.54, 136.97, 130.88, 130.15, 127.05, 126.41, 125.80, 125.63. GC-MS (EI): 157.1, 129.1, 102.1, 75.0, 63.1, 51.1, 29.1.Procedure B for Compounds 5a–z,bbHeterocycle (0.10 mmol), ammonium persulfate (0.20 mmol), [Ir{dF(CF3ppy)}2(dtbbpy)]PF6 (0.2 mol%), α-keto acids (1.0 mmol) were placed in a dry glass tube. Anhydrous DMSO (1 mL) was injected into the tube by a syringe under a N2 atmosphere. The solution was then stirred at room temperature under the irradiation of 15 W blue LEDs strip for 12 h. After completion of the reaction, saturated Na2CO3 solution was added to adjust pH to basic. The combined organic layer was washed with brine and then dried over anhydrous Na2SO4. The desired products were obtained in the corresponding yields after purification by flash chromatography on silica gel eluting with PE and EtOAc.(4-Methylquinolin-2-yl)(phenyl)methanone (5b)Brownish solid. 1H NMR (400 MHz, CDCl3): δ = 8.22 (dd, J = 14.0, 7.9 Hz, 3 H), 8.07 (d, J = 8.3 Hz, 1 H), 7.94 (s, 1 H), 7.77 (t, J = 7.6 Hz, 1 H), 7.72–7.65 (m, 1 H), 7.62 (t, J = 7.4 Hz, 1H), 7.51 (t, J = 7.7 Hz, 2H), 2.80 (s, 3 H).13C NMR (151 MHz, CDCl3): δ = 194.33, 154.52, 146.72, 145.78, 136.32, 133.18, 131.59, 131.27, 129.86, 129.08, 128.30, 128.27, 123.90, 121.43,19.08. GC-MS (EI): 247.1, 232.1, 218.1, 204.1, 140.0, 105.0, 77.1, 51.1, 28.1.