Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Organoboronic Acids

Journal of Organic Chemistry

Volumn 80, Issue 16, 2015, Pages 7856-7864

  Xia, Ying ^a   Ge, Rui ^a   Chen, Li ^a   Liu, Zhen ^a   Xiao, Qing ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL REACTIONS; ORGANIC POLLUTANTS; ORGANIC POLYMERS;

CROSS COUPLING REACTIONS; CROSS-COUPLINGS; FURAN DERIVATIVES; HYDRIDE ELIMINATION; MIGRATORY INSERTION; ORGANOBORONIC ACIDS; PALLADIUM-CATALYZED; STEREOSELECTIVE MANNER;

FINANCIAL MARKETS;

1,3 DIENE; ALKADIENE; ALKYL GROUP; ALKYNE; BORONIC ACID DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; CHEMICAL COMPOUND; ENYNONE; FURAN DERIVATIVE; HYDROGEN; ORGANOBORONIC ACID; PALLADIUM; UNCLASSIFIED DRUG; KETONE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; DENSITY FUNCTIONAL THEORY; NUCLEAR OVERHAUSER EFFECT; OXIDATIVE CROSS COUPLING; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKYNES; BORONIC ACIDS; CATALYSIS; FURANS; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM;

EID: 84939786766     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01350     Document Type: Article

References (60)

1. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 2011, 1015 10.1002/ejoc.201001588
2. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486 10.1002/anie.201007961
3. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560 10.1039/C1CS15127D
4. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236 10.1021/ar300101k
5. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586 10.1021/cs4006666
6. Kitamura, M.; Yuasa, R.; Van Vranken, D. L. Tetrahedron Lett. 2015, 56, 3027 10.1016/j.tetlet.2014.10.140
7. Zhou, P.-X.; Ye, Y.-Y.; Zhao, L.-B.; Hou, J.-Y.; Kang, X.; Chen, D.-Q.; Tang, Q.; Zhang, J.-Y.; Huang, Q.-X.; Zheng, L.; Ma, J.-W.; Xu, P.-F.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 16093 10.1002/chem.201405172
8. Aziz, J.; Frison, G.; Gómez, M.; Brion, J.-D.; Hamze, A.; Alami, M. ACS Catal. 2014, 4, 4498 10.1021/cs5014877
9. Wang, P.-S.; Lin, H.-C.; Zhou, X.-L.; Gong, L.-Z. Org. Lett. 2014, 16, 3332 10.1021/ol501356z
10. Zhou, P.-X.; Ye, Y.-Y.; Ma, J.-W.; Zheng, L.; Tang, Q.; Qiu, Y.-F.; Song, B.; Qiu, Z.-H.; Xu, P.-F.; Liang, Y.-M. J. Org. Chem. 2014, 79, 6627 10.1021/jo501125b
11. Zhou, P.-X.; Zheng, L.; Ma, J.-W.; Ye, Y.-Y.; Liu, X.-Y.; Xu, P.-F.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 6745 10.1002/chem.201402097
12. Barroso, R.; Valencia, R. A.; Cabal, M.-P.; Valdés, C. Org. Lett. 2014, 16, 2264 10.1021/ol500778u
13. Xia, Y.; Xia, Y.; Liu, Z.; Zhang, Y.; Wang, J. J. Org. Chem. 2014, 79, 7711 10.1021/jo5012703
14. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215 10.1021/cr100280d
15. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780 10.1021/cr100379j
16. Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761 10.1039/c0cs00125b
17. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588 10.1039/c2cs35096c
18. Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566 10.1021/ja0782293
19. Zhao, X.; Jing, J.; Lu, K.; Zhang, Y.; Wang, J. Chem. Commun. 2010, 46, 1724 10.1039/b925590g
20. Tsoi, Y.-T.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 4506 10.1021/ol101796t
21. Xia, Y.; Xia, Y.; Liu, Z.; Zhang, Y.; Wang, J. J. Org. Chem. 2014, 79, 7711 10.1021/jo5012703
22. Zhou, L.; Ye, F.; Ma, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 3510 10.1002/anie.201007224
23. Chen, H.; Huang, L.; Fu, W.; Liu, X.; Jiang, H. Chem.-Eur. J. 2012, 18, 10497 10.1002/chem.201200949
24. Zeng, X.; Cheng, G.; Shen, J.; Cui, X. Org. Lett. 2013, 15, 3022 10.1021/ol401217h
25. Roche, M.; Frison, G.; Brion, J.-D.; Provot, O.; Hamze, A.; Alami, M. J. Org. Chem. 2013, 78, 8485 10.1021/jo401217x
26. For a review, see: Miki, K.; Uemura, S.; Ohe, K. Chem. Lett. 2005, 34, 1068 10.1246/cl.2005.1068
27. Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260 10.1021/ja025776+
28. Miki, K.; Yokoi, T.; Nishino, F.; Kato, Y.; Washitake, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 2004, 69, 1557 10.1021/jo0352732
29. Kato, Y.; Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. Org. Lett. 2003, 5, 2619 10.1021/ol034731q
30. Miki, K.; Washitake, Y.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 2004, 43, 1857 10.1002/anie.200352949
31. González, M. J.; López, E.; Vicente, R. Chem. Commun. 2014, 50, 5379 10.1039/C3CC47481J
32. Vicente, R.; González, J.; Riesgo, L.; González, J.; López, L. Angew. Chem., Int. Ed. 2012, 51, 8063 10.1002/anie.201203914
33. González, J.; González, J.; Pérez-Calleja, C.; López, L.; Vicente, R. Angew. Chem., Int. Ed. 2013, 52, 5853 10.1002/anie.201301625
34. Song, B.; Li, L.-H.; Song, X.-R.; Qiu, Y.-F.; Zhong, M.-J.; Zhou, P.-X.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 5910 10.1002/chem.201402513
35. González, M. J.; López, L. A.; Vicente, R. Org. Lett. 2014, 16, 5780 10.1021/ol502848n
36. Wang, T.; Zhang, J. Dalton Trans. 2010, 39, 4270 10.1039/c0dt00024h
37. Ma, J.; Jiang, H.; Zhu, S. Org. Lett. 2014, 16, 4472 10.1021/ol502018d
38. Cao, H.; Zhan, H.; Cen, J.; Lin, J.; Lin, Y.; Zhu, Q.; Fu, M.; Jiang, H. Org. Lett. 2013, 15, 1080 10.1021/ol400080e
39. Zhan, H.; Lin, X.; Qiu, Y.; Du, Z.; Li, P.; Li, Y.; Cao, H. Eur. J. Org. Chem. 2013, 2013, 2284 10.1002/ejoc.201300016
40. Clark, J. S.; Boyer, A.; Aimon, A.; Engel García, P.; Lindsay, D. M.; Symington, A. D. F.; Danoy, Y. Angew. Chem., Int. Ed. 2012, 51, 12128 10.1002/anie.201207300
41. Clark, J. S.; Romiti, F.; Hogg, K. F.; Hamid, M. H. S. A.; Richter, S. C.; Boyer, A.; Redman, J. C.; Farrugia, L. J. Angew. Chem., Int. Ed. 2015, 54, 5744 10.1002/anie.201500625
42. Xia, Y.; Qu, S.; Xiao, Q.; Wang, Z.-X.; Qu, P.; Chen, L.; Liu, Z.; Tian, L.; Huang, Z.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 13502 10.1021/ja4058844
43. For a related Cu(I)-catalyzed reaction, see: Hu, F.; Xia, Y.; Ma, C.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 4082 10.1021/ol501747f
44. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295 10.1021/jo970837l
45. Hashmi, A. S. K.; Choi, J.-H.; Bats, J. W. J. Prakt. Chem. 1999, 341, 342
46. Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO;2-F
47. Hashmi, A. S. K.; Schwarz, L.; Bolte, M. (2004, 1923.
48. Sevov, C. S.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 10625 and references cited therein 10.1021/ja504414c
49. Recently, we have communicated the related Pd-catalyzed oxidative coupling with terminal alkynes; see: Xia, Y.; Liu, Z.; Ge, R.; Xiao, Q.; Zhang, Y.; Wang, J. Chem. Commun. 2015, 51, 11233 10.1039/C5CC03559G
50. Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955 10.1016/S0040-4020(97)10303-9
51. Keay, B. A. Chem. Soc. Rev. 1999, 28, 209 10.1039/a809439j
52. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850 10.1002/anie.200461668
53. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076 10.1039/b602596j
54. Moran, W. J.; Rodríguez, A. Org. Prep. Proced. Int. 2012, 44, 103 10.1080/00304948.2012.657558
55. Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 3715 10.1002/anie.201310146
56. Wang, T.; Huang, L.; Shi, S.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2014, 20, 14868 10.1002/chem.201404229
57. Xia, Y.; Xia, Y.; Ge, R.; Liu, Z.; Xiao, Q.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 3917 10.1002/anie.201400500
58. Wang, T.; Shi, S.; Rudolph, M.; Hashmi, A. S. K. Adv. Synth. Catal. 2014, 356, 2337 10.1002/adsc.201400356
59. Journet, M.; Cai, D.; DiMichele, L. M.; Larsen, R. D. Tetrahedron Lett. 1998, 39, 6427 10.1016/S0040-4039(98)01352-5
60. Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Galzerano, P.; Melchiorre, P.; Sambri, L. Tetrahedron Lett. 2008, 49, 2555 10.1016/j.tetlet.2008.02.093