Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Symmetrical Diaryl Ketones at Atmospheric CO Pressure

Yang Li; Wei Lu; Dong Xue; Chao Wang; Zhao-Tie Liu; Jianliang Xiao

doi:10.1055/s-0033-1340957

Synlett, Table of Contents

Synlett 2014; 25(08): 1097-1100
DOI: 10.1055/s-0033-1340957

letter

Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Symmetrical Diaryl Ketones at Atmospheric CO Pressure

Yang Li

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Wei Lu

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Dong Xue*

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Chao Wang

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Zhao-Tie Liu

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Jianliang Xiao*

^aKey Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

^bDepartment of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK Email: j.xiao@liverpool.ac.uk

› Author Affiliations

Abstract

All articles of this category

Abstract

A mild and efficient synthesis of symmetrical diaryl ketones by palladium-catalyzed oxidative carbonylation of arylboronic acids with carbon monoxide at atmospheric pressure is reported.

Key words

palladium - carbonylation - carbon monoxide - arylboronic acids - diaryl ketone

Full Text

References

References and Notes

For reviews, see:

1a Beller M, Cornils B, Frohning CD, Kohlpaintner CW. J. Mol. Catal. A 1995; 104: 17
1b Brunet J.-J, Chauvin R. Chem. Soc. Rev. 1995; 89
1c Brennfuehrer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
1d Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1

2a Ohe T, Ohe K, Uemura S, Sugita N. J. Organomet. Chem. 1988; 344: C5
2b Cho CS, Ohe T, Uemura S. J. Organomet. Chem. 1995; 496: 221
2c Gooβen LJ, Ghosh K. Angew. Chem. Int. Ed. 2001; 40: 3458
2d Xin B, Zhang Y, Cheng K. J. Org. Chem. 2006; 71: 5725
2e Kaganovsky L, Gelman D, Rueck-Braun K. J. Organomet. Chem. 2010; 695: 260
2f Dheur J, Sauthier M, Castanet Y, Mortreux A. Adv. Synth. Catal. 2010; 352: 557
2g Yu A, Shen L, Cui X, Peng D, Wu Y. Tetrahedron 2012; 68: 2283
2h Wu X.-F, Neumann H, Beller M. Chem. Asian J. 2012; 7: 282

3a Morera E, Ortar G. Tetrahedron Lett. 1998; 39: 2835
3b Wannberg J, Larhed M. J. Org. Chem. 2003; 68: 5750
3c Wu X, Ekegren JK, Larhed M. Organometallics 2006; 25: 1434
3d Tambade PJ, Patil YP, Bhanushali MJ, Bhanage BM. Synthesis 2008; 2347
3e Ren W, Yamane M. J. Org. Chem. 2009; 74: 8332
3f Wieckowska A, Fransson R, Odell LR, Larhed M. J. Org. Chem. 2011; 76: 978
3g Fuente VD. L, Godard C, Claver C, Castillón S. Adv. Synth. Catal. 2012; 354: 1971
3h Gong X, Miller PW, Gee AD, Long NJ, Mello AJ, Vilar R. Chem. Eur. J. 2012; 18: 2768
3i Khedlar MV, Sasaki T, Bhanage BM. ACS Catal. 2013; 3: 287

For selected examples of palladium-catalyzed carbonylations of aryl halides, see:

4a Schoenberg A, Bartoletti I, Heck RF. J. Org. Chem. 1974; 39: 3318
4b Schoenberg A, Heck RF. J. Am. Chem. Soc. 1974; 96: 7761
4c 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
4d Martinelli JR, Clark TP, Watson DA, Munday RH, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 8460
4e Sergeev AG, Spannenberg A, Beller M. J. Am. Chem. Soc. 2008; 130: 15549
4f Wu X.-F, Wu L, Jackstell R, Neumann H, Beller M. Chem. Eur. J. 2013; 19: 12245
4g Wu X.-F, Oschatz S, Sharif M, Beller M, Langer P. Tetrahedron 2014; 70: 23

5a Liu Q, Zhang H, Lei A. Angew. Chem. Int. Ed. 2011; 50: 10788
5b Wu X.-F, Neumann H, Beller M. ChemSusChem 2013; 6: 229

6 Wu X.-F, Neumann H, Beller M. Chem. Asian J. 2012; 7: 282

7a Kuş M, Artok ÖA, Ziyanak F, Artok L. Synlett 2008; 2587
7b Artok L, Kuş M, Aksın-Artok Ö, Dege FN, Özkılınç FY. Tetrahedron 2009; 65: 9125

8 Liu Q, Li G, He J, Liu J, Li P, Lei A. Angew. Chem. Int. Ed. 2010; 49: 3371

For recent examples, see:

9a Tantama M, Lin W.-C, Licht S. J. Am. Chem. Soc. 2008; 130: 15766
9b Lam OP, Anthon C, Heinemann FW, O’Connor JM, Meyer K. J. Am. Chem. Soc. 2008; 130: 6567
9c Hagberg DP, Yum J.-H, Lee H.-J, De Angelis F, Marinado T, Karlsson KM, Humphry-Baker R, Sun L, Hagfeldt A, Graetzel M, Nazeeruddin MK. J. Am. Chem. Soc. 2008; 130: 6259
9d Papageorgiou G, Ogden D, Corrie JE. T. Photochem. Photobiol. Sci. 2008; 7: 423
9e Liu L, Zhang G, Xiang J, Zhang D, Zhu D. Org. Lett. 2008; 10: 4581
9f Dumur F, Mayer CR, Dumas E, Miomandre F, Frigoli M, Secheresse F. Org. Lett. 2008; 10: 321
9g Seo JW, Kim HJ, Lee BS, Katzenellenbogen JA, Chi DY. J. Org. Chem. 2008; 73: 715
9h Albrecht K, Yamamoto K. J. Am. Chem. Soc. 2009; 131: 2244
9i Claramunt RM, Lopez C, Perez-Medina C, Perez-Torralba M, Elguero J, Escames G, Acuna-Castroviejo D. Bioorg. Med. Chem. 2009; 17: 6180
9j Navale TS, Zhai L, Lindeman SV, Rathore R. Chem. Commun. 2009; 2857
9k Rueping M, Vila C, Szadkowska A, Koenigs RM, Fronert J. ACS Catal. 2012; 2: 2810
9l Suzuki Y, Iinurm M, Moriyama K, Togo H. Synlett 2012; 23: 1250

For recent examples, see:

10a Vooturi SK, Cheung CM, Rybak MJ, Firestine SM. J. Med. Chem. 2009; 52: 5020
10b Plazuk D, Vessieres A, Hillard EA, Buriez O, Labbe E, Pigeon P, Plamont M.-A, Amatore C, Zakrzewski J, Jaouen G. J. Med. Chem. 2009; 52: 4964
10c Luque-Ortega JR, Reuther P, Rivas L, Dardonville C. J. Med. Chem. 2010; 53: 1788
10d Choy PY, Kwong FY. Org. Lett. 2013; 15: 270

For recent examples, see:

11a Dewal MB, Xu Y, Yang J, Mohammed F, Smith MD, Shimizu LS. Chem. Commun. 2008; 3909
11b Kim H, So SM, Yen CP.-H, Vinhato E, Lough AJ, Hong J.-I, Kim H.-J, Chin J. Angew. Chem. Int. Ed. 2008; 47: 8657
11c Fukuda M, Sekiya R, Kuroda R. Angew. Chem. Int. Ed. 2008; 47: 706
11d Yang H.-B, Ghosh K, Zhao Y, Northrop BH, Lyndon MM, Muddiman DC, White HS, Stang PJ. J. Am. Chem. Soc. 2008; 130: 839
11e Ruhland K, Obenhuber A, Hoffmann SD. Organometallics 2008; 27: 3482
11f Qin Q, Mague JT, Pascal RA. Jr. Org. Lett. 2010; 12: 928
11g Safin DA, Babashkina MG, Bolte M, Garcia Y. Polyhedron 2013; 62: 133

For recent examples, see:

12a Tanaka D, Nakagawa K, Higuchi M, Horike S, Kubota Y, Kobayashi TC, Takata M, Kitagawa S. Angew. Chem. Int. Ed. 2008; 47: 3914
12b Peng H. J. Am. Chem. Soc. 2008; 130: 42
12c Wang D, Zhang S, Zhang Y, Wang H, Mu J, Wang G, Jiang Z. Dyes Pigm. 2008; 79: 217
12d Kizilkaya C, Karatas S, Apohan N.-K, Guengoer A. J. Appl. Polym. Sci. 2010; 115: 3256

13a Olah GA In Friedel–Crafts and Related Reactions. Wiley; New York: 1963
13b Olah GA In Friedel–Crafts Chemistry. Wiley; New York: 1973
13c Bandini M, Melloni A, Umani-Ronchi A. Angew. Chem. Int. Ed. 2004; 43: 550

14a Yu A, Li J, Cui M, Wu Y. Synlett 2007; 3063
14b Qureshi ZS, Deshmukh KM, Tambade PJ, Bhanage BM. Synthesis 2011; 243

15a Gooβen LJ, Ghosh K. Angew. Chem. Int. Ed. 2001; 40: 3458
15b Shen X.-B, Gao T.-T, Lu J.-M, Shao L.-X. Appl. Organometal Chem. 2011; 25: 497

16 Ishiyama T, Kizaki H, Miyaura N, Suzuki A. Tetrahedron Lett. 1993; 34: 7595

17a Tambade PJ, Patil YP, Panda AG, Bhanage BM. Eur. J. Org. Chem. 2009; 3022
17b Kaganovsky L, Gelman D, Rueck-Braun K. J. Organomet. Chem. 2010; 695: 260
17c Khedkar MV, Tambade PJ, Qureshi ZS, Bhanage BM. Eur. J. Org. Chem. 2010; 6981
17d Gong X, Miller PW, Gee AD, Long NJ, Mello AJ, Vilar R. Chem. Eur. J. 2012; 18: 2768
17e Wu X.-F, Neumann H, Beller M. Adv. Synth. Catal. 2011; 353: 788
17f Li H.-L, Yang M, Qi Y.-X, Xue J.-J. Eur. J. Org. Chem. 2011; 2662
17g Liu J, Zhou X.-Y, Rao H.-H, Xiao F.-H, Li C.-J, Deng G.-J. Chem. Eur. J. 2011; 17: 7996

18 Li Y, Xue D, Wang C, Liu Z.-T, Xiao J. Chem. Commun. 2012; 48: 1320

19a Du X, Suguro M, Hirabayashi K, Mori A. Org. Lett. 2001; 3: 3313
19b Jung YC, Mishra RK, Yoon CH, Jung KW. Org. Lett. 2003; 5: 2231
19c Yoon CH, Yoo KS, Yi SW, Mishra RK, Jung KW. Org. Lett. 2004; 6: 4037
19d Andappan MM. S, Nilsson P, Larhed M. Chem. Commun. 2004; 218
19e Andappan MM. S, Nilsson P, von Schenck H, Larhed M. J. Org. Chem. 2004; 69: 5212
19f Yoo KS, Yoon CH, Jung KW. J. Am. Chem. Soc. 2006; 128: 16384
19g Akiyama K, Wakabayashi K, Mikami K. Adv. Synth. Catal. 2005; 347: 1569
19h Ruan J, Li X, Saidi O, Xiao J. J. Am. Chem. Soc. 2008; 130: 2424

20a Dunlop RD, Gardener JH. J. Am. Chem. Soc. 1933; 55: 1665
20b Adams DJ, Clark JH, McFarland H. J. Fluorine Chem. 1998; 92: 127

21 Searle OB, Pfeiffer RH. Polym. Eng. Sci. 1985; 25: 474
22 General Procedure for the Carbonylation of Arylboronic Acids The reaction was carried out in an autoclave containing a 10 mL Teflon reaction tube. Pd(PPh₃)₄ (0.02 mmol), DPPP (0.04 mmol), and a magnetic stir bar were placed in the tube which was then capped with a stopper and flushed with argon. Then, aryl boronic acid (1 mmol), AgNO₃ (1 mmol), and acetone (3 mL) were added to the tube. The tube was put into the autoclave. Once sealed, the autoclave was purged several times with CO, pressurized to 1 atm at r.t. and then heated in an oil bath at 40 °C for 24 h. The autoclave was then cooled to r.t. and carefully vented to discharge CO in a fume hood. Water (10 mL) was added, and the product was extracted with CH₂Cl₂ (3 × 15 mL). The organic layers were washed with brine, dried over Na₂SO₄, and evaporated. The crude product was purified by column chromatography on silica gel using a mixture of EtOAc and PE as eluent to give the products. The identity and purity of the product was confirmed by ¹H NMR and ¹³C NMR spectroscopy and MS or HRMS spectrometry. Benzophenone (2a) R_f = 0.3 (PE–EtOAc, 50:1), yellow oil. ¹H NMR (400 MHz, CDCl₃): δ = 7.83 (d, J = 7.6 Hz, 4 H), 7.62 (t, J = 7.2 Hz, 2 H), 7.51 (t, J = 7.6 Hz, 4 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 196.8, 137.6, 132.4, 130.1, 130.0, 128.3, 128.3 ppm. IR (KBr): 3040, 1658, 1603, 1321, 1274 cm^–1. ESI-HRMS: m/z calcd for [M + Na⁺]: 205.0621; found: 205.0624. Bis(4-fluorophenyl)meyhanone (2b) R_f = 0.3 (PE–EtOAc, 50:1), light yellow soild; mp 87–88 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.76–7.72 (m, 4 H), 7.11–7.07 (m, 4 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 193.7, 165.4 (d, J _C–F = 252.9 Hz), 133.7 (d, J _C–F = 3 Hz), 132.4 (d, J _C–F = 9.1 Hz), 115.5 (d, J _C–F = 21.8 Hz) ppm. IR (KBr): 1647, 1496, 1295, 953, 760 cm^–1. ESI-HRMS: m/z calcd for [M + Na⁺]: 241.0442; found: 241.0435. Bis(4-chlorophenyl)methanone (2c) R_f = 0.3 (PE–EtOAc, 50:1), solid; mp 127–128 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.72 (d, J = 8.4 Hz, 4 H), 7.46 (d, J = 8.4 Hz, 4 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 193.1, 138.1, 134.5, 130.3, 127.8 ppm. IR (KBr): 2364, 1651, 1585, 1275, 841, 756 cm^–1. ESI-HRMS: m/z calcd for [M + Na⁺]: 272.9851; found: 272.9844.

Supplementary Material

Supporting Information