Photoredox-Catalyzed Decarboxylative C–H Acylation of Heteroarenes

Wei Jia; Yong Jian; Binbin Huang; Chao Yang; Wujiong Xia

doi:10.1055/s-0037-1609911

Synlett, Table of Contents

Synlett 2018; 29(14): 1881-1886
DOI: 10.1055/s-0037-1609911

letter

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

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Abstract

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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

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References

References and Notes

1a Baumann KL. Butler DE. Deering CF. Mennen KE. Millar A. Nanninga TN. Palmer CW. Roth BD. Tetrahedron Lett. 1992; 33: 2283
1b Fráter G. Bajgrowicz JA. Kraft P. Tetrahedron 1998; 54: 7633
1c Magnus P. Sane N. Fauber BP. Lynch V. J. Am. Chem. Soc. 2009; 131: 16045
1d McNamara JM. Leazer JL. Bhupathy M. Amato JS. Reamer RA. Reider PJ. Grabowski EJ. J. J. Org. Chem. 1989; 54: 3718
1e Murakami K. Yamada S. Kaneda T. Itami K. Chem. Rev. 2017; 117: 9302
1f Schwarz J. Konig B. Green Chem. 2018; 20: 323
1g Woodward RB. Cava MP. Ollis WD. Hunger A. Daeniker HU. Schenker K. J. Am. Chem. Soc. 1954; 76: 4749

2a Alberico D. Scott ME. Lautens M. Chem. Rev. 2007; 107: 174
2b Cheng C. Hartwig JF. Chem. Rev. 2015; 115: 8946
2c Liu C. Yuan J. Gao M. Tang S. Li W. Shi R. Lei A. Chem. Rev. 2015; 115: 12138

3a Antonchick AP. Burgmann L. Angew. Chem. Int. Ed. 2013; 52: 3267
3b Minisci F. Vismara E. Fontana F. J. Org. Chem. 1989; 54: 5224
3c Molander GA. Colombel V. Braz VA. Org. Lett. 2011; 13: 1852

4a Falbe J. Regitz M. Römpp Chemie Lexikon. Thieme; Stuttgart: 1995
4b Pattenden G. Crawford LP. Richardson SK. Aldehydes and Ketones, In General and Synthetic Methods 1994; Vol. 16: 37
4c Taddei M. Mann A. Hydroformylation for Organic Synthesis. Vol. 342. Springer; Berlin, Heidelberg: 2013

5a Crounse NN. The Gattermann–Koch Reaction. In Organic Reactions. Vol. 5. John Wiley and Sons; 1949: 290
5b Duff JC. Bills EJ. J. Chem. Soc. 1932; 1987
5c Jones G. Stanforth SP. The Vilsmeier Reaction of Non-Aromatic Compounds. In Organic Reactions. Vol. 56. John Wiley and Sons; 2000: 355
5d Wynberg H. Chem. Rev. 1960; 60: 169

6 Bouveault L. Bull. Soc. Chim. Fr. 1904; 31: 1306

7a Baillargeon VP. Stille JK. J. Am. Chem. Soc. 1986; 108: 452
7b Brennführer A. Neumann H. Beller M. Synlett 2007; 2537
7c Klaus S. Neumann H. Zapf A. Strübing D. Hübner S. Almena J. Riermeier T. Groß P. Sarich M. Krahnert W.-R. Rossen K. Beller M. Angew. Chem. Int. Ed. 2006; 45: 154
7d Korsager S. Taaning RH. Skrydstrup T. J. Am. Chem. Soc. 2013; 135: 2891
7e Natte K. Dumrath A. Neumann H. Beller M. Angew. Chem. Int. Ed. 2014; 53: 10090
7f Natte K. Dumrath A. Neumann H. Beller M. Angew. Chem. 2014; 126: 10254
7g Pri-Bar I. Buchman O. J. Org. Chem. 1984; 49: 4009
7h Ueda T. Konishi H. Manabe K. Angew. Chem. Int. Ed. 2013; 52: 8611
7i Yu B. Zhao Y. Zhang H. Xu J. Hao L. Gao X. Liu Z. Chem. Commun. 2014; 50: 2330

8 Schoenberg A. Bartoletti I. Heck RF. J. Org. Chem. 1974; 39: 3318

9a Duncton MA. J. MedChemComm 2011; 2: 1135
9b Fontana F. Minisci F. Nogueira Barbosa MC. Vismara E. J. Org. Chem. 1991; 56: 2866
9c Minisci F. Synthesis 1973; 1
9d Minisci F. Fontana F. Vismara E. J. Heterocycl. Chem. 1990; 27: 79
9e Tauber J. Imbri D. Opatz T. Molecules 2014; 19: 16190

10a Kärkäs MD. Porco JA. Stephenson CR. J. Chem. Rev. 2016; 116: 9683
10b Ravelli D. Protti S. Fagnoni M. Chem. Rev. 2016; 116: 9850
10c Romero NA. Nicewicz DA. Chem. Rev. 2016; 116: 10075
10d Skubi KL. Blum TR. Yoon TP. Chem. Rev. 2016; 116: 10035
10e Chen J.-R. Hu X.-Q. Lu L.-Q. Xiao W.-J. Acc. Chem. Res. 2016; 49: 1911
10f Ghosh I. Marzo L. Das A. Shaikh R. König B. Acc. Chem. Res. 2016; 49: 1566
10g Tellis JC. Kelly CB. Primer DN. Jouffroy M. Patel NR. Molander GA. Acc. of Chem. Res. 2016; 49: 1429

11a Candish L. Standley EA. Gómez-Suárez A. Mukherjee S. Glorius F. Chem. Eur. J. 2016; 22: 9971
11b Cassani C. Bergonzini G. Wallentin C.-J. Org. Lett. 2014; 16: 4228
11c Chu L. Ohta C. Zuo Z. MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 10886
11d Gao F. Wang J.-T. Liu L.-L. Ma N. Yang C. Gao Y. Xia W. Chem. Commun. 2017; 53: 8533
11e Garza-Sanchez RA. Tlahuext-Aca A. Tavakoli G. Glorius F. ACS Catal. 2017; 7: 4057
11f Griffin JD. Zeller MA. Nicewicz DA. J. Am. Chem. Soc. 2015; 137: 11340
11g Johnston CP. Smith RT. Allmendinger S. MacMillan DW. C. Nature 2016; 536: 322
11h Liu J. Liu Q. Yi H. Qin C. Bai R. Qi X. Lan Y. Lei A. Angew. Chem. Int. Ed. 2014; 53: 502
11i Noble A. MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 11602
11j Noble A. McCarver SJ. MacMillan DW. C. J. Am. Chem. Soc. 2015; 137: 624
11k Rueda-Becerril M. Mahé O. Drouin M. Majewski MB. West JG. Wolf MO. Sammis GM. Paquin J.-F. J. Am. Chem. Soc. 2014; 136: 2637
11l Ventre S. Petronijevic FR. MacMillan DW. C. J. Am. Chem. Soc. 2015; 137: 5654
11m Xuan J. Zhang Z.-G. Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 15632
11n Zhou Q.-Q. Guo W. Ding W. Wu X. Chen X. Lu L.-Q. Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 11196
11o Zuo Z. Ahneman DT. Chu L. Terrett JA. Doyle AG. MacMillan DW. C. Science 2014; 345: 437
11p Zuo Z. MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 5257
11q Sherwood TC. Li N. Yazdani AN. Dhar TG. M. J. Org. Chem. 2018; 83: 3000

12 Huang H. Li X. Yu C. Zhang Y. Mariano PS. Wang W. Angew. Chem. Int. Ed. 2017; 56: 1500
13 Nielsen MK. Shields BJ. Liu J. Williams MJ. Zacuto MJ. Doyle AG. Angew. Chem. Int. Ed. 2017; 56: 7191
14 Ji W. Li P. Yang S. Wang L. Chem. Commun. 2017; 53: 8482
15 Li X. Gu X. Li Y. Li P. ACS Catal. 2014; 4: 1897

16a Cheng W.-M. Shang R. Fu M.-C. Fu Y. Chem. Eur. J. 2017; 23: 2537
16b Cheng W.-M. Shang R. Fu Y. ACS Catal. 2017; 7: 907
16c DiRocco DA. Dykstra K. Krska S. Vachal P. Conway DV. Tudge M. Angew. Chem. Int. Ed. 2014; 53: 4802
16d Huff CA. Cohen RD. Dykstra KD. Streckfuss E. DiRocco DA. Krska SW. J. Org. Chem. 2016; 81: 6980
16e Jin J. MacMillan DW. C. Nature 2015; 525: 87
16f Kammer LM. Rahman A. Opatz T. Molecules 2018; 23: 764
16g Sherwood TC. Li N. Yazdani AN. Dhar TG. M. J. Org. Chem. 2018; 83: 3000

17 Gutiérrez-Bonet Á. Remeur C. Matsui JK. Molander GA. J. Am. Chem. Soc. 2017; 139: 12251
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.

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