Nano-Pd/Al(OH)3-Catalyzed Suzuki–Miyaura Coupling Reaction of Potassium Aryl- and Heteroaryltrifluoroborates with Electrophiles in Alcohols

Tingting Zhu; Xing Li; Honghong Chang; Wenchao Gao; Wenlong Wei

doi:10.1055/s-0035-1561302

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(06): 880-887
DOI: 10.1055/s-0035-1561302

letter

Nano-Pd/Al(OH)₃-Catalyzed Suzuki–Miyaura Coupling Reaction of Potassium Aryl- and Heteroaryltrifluoroborates with Electrophiles in Alcohols

Tingting Zhu

Department of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: weiwenlong@tyut.edu.cn eMail: lixing@tyut.edu.cn

,

Xing Li*

Department of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: weiwenlong@tyut.edu.cn eMail: lixing@tyut.edu.cn

,

Honghong Chang

Department of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: weiwenlong@tyut.edu.cn eMail: lixing@tyut.edu.cn

,

Wenchao Gao

Department of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: weiwenlong@tyut.edu.cn eMail: lixing@tyut.edu.cn

,

Wenlong Wei*

Department of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: weiwenlong@tyut.edu.cn eMail: lixing@tyut.edu.cn

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Abstract

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Abstract

Highly active aluminium hydroxide supported nanopalladium-catalyzed Suzuki–Miyaura coupling reactions of potassium aryl- and heteroaryltrifluoroborates with aryldiazonium salts or aromatic, heteroaromatic halides have been achieved, respectively. Most substrates were shown to cross-couple with ease to aryl compounds as well as to a variety of heteroaromatic bromides in good to excellent yields.

Key words

Pd/Al(OH)₃ - Suzuki–Miyaura - potassium aryltrifluoroborates - aryldiazonium tetrafluoroborate salts - aryl halides

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Referenzen

References and Notes

For recent reviews on the coupling reactions with organoboron compounds, see:

1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
1b Suzuki A In Metal-Catalyzed Cross-Coupling Reactions. Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 49-97
1c Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275
1d Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
1e Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
1f Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
1g Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6723

For recent selected examples, see:

2a Sengupta S, Bhattacharyya S. J. Org. Chem. 1997; 62: 3405
2b Suzuki A. J. Organomet. Chem. 1999; 576: 147
2c Quach TD, Batey RA. Org. Lett. 2003; 5: 4397
2d Fang G.-H, Yan Z.-J, Deng M.-Z. Org. Lett. 2004; 6: 357
2e Molander GA, Fumagalli T. J. Org. Chem. 2006; 71: 5743
2f Molander GA, Sandrock DL. Org. Lett. 2007; 9: 1597
2g Dreher SD, Dormer PG, Sandrock DL, Molander GA. J. Am. Chem. Soc. 2008; 130: 9257
2h Dreher SD, Lim SE, Sandrock DL, Molander GA. J. Org. Chem. 2009; 74: 3626
2i Molander GA, Gormisky PE, Sandrock DL. J. Org. Chem. 2008; 73: 2052
2j Molander GA, Vargas F. Org. Lett. 2007; 9: 203

For selected Cu-catalyzed reactions, see:

3a Quach TD, Batey RA. Org. Lett. 2003; 5: 1381
3b Bolshan Y, Batey RA. Angew. Chem. Int. Ed. 2008; 47: 2109
3c Gurung SK, Thapa S, Kafle A, Dickie DA, Giri R. Org. Lett. 2014; 16: 1264

For selected Ni-catalyzed reactions, see:

3d Molander GA, Argintaru OA, Aron I, Dreher SD. Org. Lett. 2010; 12: 5783
3e Zhang N, Hoffman DJ, Gutsche N, Gupta J, Percec V. J. Org. Chem. 2012; 77: 5956

For selected Rh-catalyzed reactions, see:

3f Luo Y, Hepburn HB, Chotsaeng N, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 8309

For selected Pd-catalyzed reactions, see:

3g Zhang C, Huang J, Trudell ML, Nolan SP. J. Org. Chem. 1999; 64: 3804
3h Molander GA, Biolatto B. Org. Lett. 2002; 4: 1867
3i Navarro O, Kelly RA. III, Nolan SP. J. Am. Chem. Soc. 2003; 125: 16194
3j Molander GA, Elia MD. J. Org. Chem. 2006; 71: 9198

For selected Fe-promoted reactions, see:

3k Wen J, Qin S, Ma L.-F, Dong L, Zhang J, Liu S.-S, Duan Y.-S, Chen S.-Y, Hu C.-W, Yu X.-Q. Org. Lett. 2010; 12: 2694

For selected Au-catalyzed reaction, see:

3l Han J, Liu Y, Guo R. J. Am. Chem. Soc. 2009; 131: 2060

4 For recent reviews about complex-catalyzed reactions, see ref. 1f and: Dupont J, Consorti CS, Spencer J. Chem. Rev. 2005; 105: 2527

For recent selected Pd complex catalyzed examples, see ref. 2f and:

5a Andrus MB, Song C. Org. Lett. 2001; 3: 3761
5b Dubbaka SR, Vogel P. Org. Lett. 2004; 6: 95
5c Barder TE, Buchwald SL. Org. Lett. 2004; 6: 2649
5d Molander GA, Petrillo DE, Landzberg NR, Rohanna JC, Biolatto B. Synlett 2005; 1763
5e Molander GA, Brown AR. J. Org. Chem. 2006; 71: 9681
5f Molander GA, Jean-Gérard L. J. Org. Chem. 2009; 74: 1297
5g Molander GA, Jean-Gérard L. J. Org. Chem. 2009; 74: 5446
5h Molander GA, Canturk B, Kennedy LE. J. Org. Chem. 2009; 74: 973
5i Kim D.-S, Ham J. Org. Lett. 2010; 12: 1092
5j Chow WK, So CM, Lau CP, Kwong FY. J. Org. Chem. 2010; 75: 5109
5k Colombel V, Rombouts F, Oehlrich D, Molander GA. J. Org. Chem. 2012; 77: 2966
5l Wong SM, So CM, Chung KH, Luk CH, Lau CP, Kwong FY. Tetrahedron Lett. 2012; 53: 3754
5m Molander GA, Wisniewski SR. J. Am. Chem. Soc. 2012; 134: 16856
5n Yuen OY, Wong SM, Chan KF, So CM, Kwong FY. Synthesis 2014; 46: 2826
5o Xiao Y.-L, Zhang B, Feng Z, Zhang X.-G. Org. Lett. 2014; 16: 4822
5p Molander GA, Rivero MR. Org. Lett. 2002; 4: 107
5q Molander GA, Gormisky PE. J. Org. Chem. 2008; 73: 7481

For recent reviews about palladium nanoparticle catalyzed reactions, see:

6a Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
6b Fihri A, Bouhrara M, Nekoueishahraki B, Basset J.-M, Polshettiwar V. Chem. Rev. Soc. 2011; 40: 5181
6c Shi JL. Chem. Rev. 2013; 113: 2139

7a Garrett CE, Prasad K. Adv. Synth. Catal. 2004; 346: 889
7b Lu F, Ruiz J, Astruc D. Tetrahedron Lett. 2004; 45: 9443
7c Wang L, Li P.-H. Chin. J. Chem. 2006; 24: 770
7d Masllorens J, González I, Roglans A. Eur. J. Org. Chem. 2007; 158
7e Jin M.-J, Lee D.-H. Angew. Chem. Int. Ed. 2010; 49: 1119

8 Molnár A. Chem. Rev. 2011; 111: 2251

For recent selected examples, see:

9a Herrmann WA, Reisinger C.-P, Spiegler M. J. Organomet. Chem. 1998; 557: 93
9b Zhang C, Trudell ML. Tetrahedron Lett. 2000; 41: 595
9c Wu L, Li B.-L, Huang Y.-Y, Zhou H.-F, He Y.-M, Fan Q.-H. Org. Lett. 2006; 8: 3605
9d Kovala-Demertzi D, Kourkoumelis N, Derlat K, Michalak J, Andreadaki FJ, Kostas ID. Inorg. Chim. Acta 2008; 361: 1562

10 Darses S, Genet J.-P. Chem. Rev. 2008; 108: 288

For recent reviews and selected examples on the coupling reactions with RBF₃K salts, see ref. 3h and:

11a Molander GA, Yun C.-S, Ribagorda M, Biolatto B. J. Org. Chem. 2003; 68: 5534
11b Darses S, Genet J.-P. Eur. J. Org. Chem. 2003; 4313
11c Kabalka GW, Al-Masum M. Tetrahedron Lett. 2005; 46: 6329
11d Cella R, Cunha RL. O. R, Reis AE. S, Pimenta DC, Klitzke CF, Stefani HA. J. Org. Chem. 2006; 71: 244
11e Wu J, Zhang L, Xia H.-G. Tetrahedron Lett. 2006; 47: 1525
11f Wu J, Zhang L, Luo Y. Tetrahedron Lett. 2006; 47: 6747
11g Arvela RK, Leadbeater NE, Mack TL, Kormos CM. Tetrahedron Lett. 2006; 47: 217
11h Kabalka GW, Zhou L.-L, Naravane A. Tetrahedron Lett. 2006; 47: 6887
11i Zhang L, Meng T, Wu J. J. Org. Chem. 2007; 72: 9346
11j Huang H, Jia K, Chen Y. Angew. Chem. Int. Ed. 2015; 54: 1881

For recent selected examples, see ref. 11g and:

12a Molander GA, Biolatto B. J. Org. Chem. 2003; 68: 4302
12b LeBlond CR, Butler KM, Ferrington MW, Browe MA. Synth. Commun. 2009; 39: 636
12c Zhao J.-L, Zhang Y.-H, Cheng K. J. Org. Chem. 2008; 73: 7428
12d Kuriyama M, Shimazawa R, Enomoto T, Shirai R. J. Org. Chem. 2008; 73: 6939
12e Harker RL, Crouch RD. Synthesis 2007; 25
12f Ren W, Li J, Zou D, Wu Y, Wu Y. Tetrahedron 2012; 68: 1351
12g Liu LF, Dong Y, Pang B, Ma JH. J. Org. Chem. 2014; 79: 7193
12h Batey RA, Quach TD. Tetrahedron Lett. 2001; 42: 9099
12i Alacid E, Nájera C. Org. Lett. 2008; 10: 5011
12j Vieria AS, Cunha RL, Klitzke CF, Zukerman-Schpector J, Stefani HA. Tetrahedron 2010; 66: 773
12k Civivos JF, Gholinejad M, Alonso DA, Nájera C. Chem. Lett. 2011; 40: 907
12l Masuyama Y, Sugioka Y, Chonan S, Suzuki N, Fujita M, Hara K, Fukuoka A. J. Mol. Catal. A: Chem. 2012; 352: 81
12m Gallo V, Mastrorilli P, Nobile CF, Paolillo R, Taccardi N. Eur. J. Inorg. Chem. 2005; 582
12n Liu L, Dong Y, Tang N. Green Chem. 2014; 16: 2185
12o Joliton A, Carreira EM. Org. Lett. 2013; 15: 5147
12p Colombel V, Presset M, Oehlrich D, Rombouts F, Molander GA. Org. Lett. 2012; 14: 1680
12q Tan J.-J, Chen Y.-G, Li H.-M, Yasuda N. J. Org. Chem. 2014; 79: 8871

13a Cacchi S, Caponetti E, Casadei MA, Giulio AD, Fabrizi G, Forte G, Goggiamani A, Moreno S, Paolicelli P, Petrucci F. Green Chem. 2012; 14: 317
13b Gómez-Martínez M, Buxaderas E, Pastor IM, Alonso DA. J. Mol. Catal. A: Chem. 2015; 404: 1

14a Li X, Yan X.-Y, Chang H.-H, Wang L.-C, Zhang Y, Chen W.-W, Li Y.-W, Wei W.-L. Org. Biomol. Chem. 2012; 10: 495
14b Li X, Wang L.-C, Chang H.-H, Zhang C.-X, Wei W.-L. Appl. Catal. A: Gen. 2013; 462-463: 15

15 Kwon MS, Kim N, Park CM, Lee JS, Kang KY, Park J. Org. Lett. 2005; 7: 1077
16 The optimal reaction conditions are as follows: Pd catalyst (0.1 mol%) and stirring for 6 h at 25 °C in MeOH (1.0 mL).
17 General Procedure for Suzuki–Miyaura Coupling of 4-Bromobenzenediazonium Tetrafluoroborate Salt with Potassium Phenyltrifluoroborate: To a tube equipped with a magnetic stir bar were added the Pd catalyst 1 (4.8 mg, 0.1 mol% Pd), 4-bromobenzenediazonium tetrafluoroborate salt 1a (0.2 mmol) and potassium phenyltrifluoroborate 2a (1.1 equiv, 0.22 mmol) in turn. Subsequently, the solvent (MeOH, 1.0 mL) was added under air atmosphere. The reaction system was then stirred at r.t. until the substrate was completely consumed as determined by TLC. The reaction mixture was purified by silica gel column chromatography to afford the desired pure coupling product 4b
18 Extensive screening showed that the optimized reaction conditions were 0.2-mmol scale of 2a with 3a (1.1 equiv) in the presence of KOAc (4.0 equiv) under air atmosphere in 0.5 mL of PEG-200 at 90 °C.
19 General Procedure for Suzuki–Miyaura Coupling Reactions of 4-Methoxybromobenzene with Potassium Phenyltrifluoroborate: To a tube equipped with a magnetic stir bar were added the Pd catalyst 1 (8.7 mg, 0.18 mol% Pd), KOAc (4.0 equiv, 78.4 mg, 0.8 mmol), potassium phenyltrifluoroborate 2a (0.2 mmol) and 4-methoxybromobenzene 3a (1.1 equiv, 0.22 mmol) in turn. Subsequently, the solvent (PEG-200, 1.0 mL) was added under air atmosphere. The reaction system was then heated to 90 °C and stirred until the substrate was completely consumed as determined by TLC. The reaction mixture was purified by silica gel column chromatography to afford the desired pure coupling product 4l.

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