De novo synthesis of γ,γ-disubstituted butyrolactones through a visible light photocatalytic arylation-lactonization sequence

Advanced Synthesis and Catalysis

Volumn 356, Issue 13, 2014, Pages 2787-2793

  Guo, Wei ^a   Cheng, Hong Gang ^a   Chen, Li Yan ^a   Xuan, Jun ^a   Feng, Zhu Jia ^a   Chen, Jia Rong ^a   Lu, Liang Qiu ^a   Xiao, Wen Jing ^a,b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b Chemical Engineering Research Center   (China)

Author keywords

Diazonium salts; Lactone synthesis; Olefinic carboxylic acids; Photocatalysis; Tandem reactions

Indexed keywords

EID: 84908458280     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400041     Document Type: Article

References (79)

1. M. Seitz, O. Reiser, Curr. Opin. Chem. Biol. 2005, 9, 285-292.
2. E. G. McMahon, Curr. Opin. Pharmacol. 2001, 1, 190.
3. a) J.-M. Huang, R. Yokoyama, C.-S. Yang, Y. Fukuyama, Tetrahedron Lett. 2000, 41, 6111-6114;
4. b) J.-M. Huang, C.-S. Yang, M. Tanaka, Y. Fukuyama, Tetrahedron 2001, 57, 4691-4698.
5. a) R. A. Pilli, G. B. Rosso, M. C. F. de Oliveira, Nat. Prod. Rep. 2010, 27, 1908-1937;
6. b) R. A. Pilli, M. C. F. de Oliveira, Nat. Prod. Rep. 2000, 17, 117-127;
7. c) Y. Ye, G.-W. Qin, R.-S. Xu, J. Nat. Prod. 1994, 57, 665-669.
8. a) S. Gil, M. Parra, P. Rodriguez, J. Segura, Mini-Rev. Org. Chem. 2009, 6, 345-358;
9. b) S. S. C. Koch, A. R. Chamberlin, in: Stud. Nat. Prod. Chem., Vol. 16, Part J, (Ed.: Atta-ur-Rahman), Elsevier, 1995, pp 687-725;
10. c) W.-Y. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417-423;
11. d) C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331-6334;
12. Angew. Chem. Int. Ed. 2004, 43, 6205-6208;
13. e) E. Wada, M. Yoshinaga, Tetrahedron Lett. 2003, 44, 7953-7956;
14. f) S. K. Mandal, S. R. Amin, W. E. Crowe, J. Am. Chem. Soc. 2001, 123, 6457-6458;
15. g) M.-H. Xu, W. Wang, G.-Q. Lin, Org. Lett. 2000, 2, 2229-2232;
16. h) B. E. Ali, H. Alper, Synlett 2000, 161-171;
17. i) N. Chatani, M. Tobisu, T. Asaumi, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1999, 121, 7160-7161;
18. j) P. Cao, X. Zhang, J. Am. Chem. Soc. 1999, 121, 7708-7709;
19. k) S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, K. Mutoh, J. Am. Chem. Soc. 1997, 119, 1482-1483;
20. l) N. M. Kablaoui, F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 4424-4431;
21. m) G. Kachkovskyi, C. Faderl, O. Reiser, Adv. Synth. Catal. 2013, 355, 2240-2248.
22. n) X.-J. Wei, D.-T. Yang, L. Wang, T. Song, L.-Z. Wu, Q. Liu, Org. Lett. 2013, 15, 6054-6057.
23. a) C.-G. Yang, N. W. Reich, Z. Shi, C. He, Org. Lett. 2005, 7, 4553-4556;
24. b) Y. Zhou, L. K. Woo, R. J. Angelici, Appl. Catal. A 2007, 333, 238-244;
25. c) D. S. Hamilton, D. A. Nicewicz, J. Am. Chem. Soc. 2012, 134, 18577-18580.
26. a) X. Zou, F. Wu, Y. Shen, S. Xu, W. Huang, Tetrahedron 2003, 59, 2555-2560;
27. b) R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462-12465;
28. c) R. Zhu, S. L. Buchwald, Angew. Chem. 2013, 125, 12887-12890;
29. Angew. Chem. Int. Ed. 2013, 52, 12655-12658.
30. D. Karila, L. Leman, R. H. Dodd, Org. Lett. 2011, 13, 5830-5833.
31. a) S. Ranganathan, K. M. Muraleedharan, N. K. Vaish, N. Jayaraman, Tetrahedron 2004, 60, 5273-5308;
32. b) S. A. Snyder, D. S. Treitler, A. P. Brucks, Aldrichimica Acta 2011, 44, 27-40.
33. a) H. Qrareya, C. Raviola, S. Protti, M. Fagnoni, A. Albini, J. Org. Chem. 2013, 78, 6016-6024;
34. b) G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 1474-1475;
35. c) S. Protti, M. Fagnoni, A. Albini, J. Am. Chem. Soc. 2006, 128, 10670-10671.
36. a) L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc. Chem. Res. 2012, 45, 1278-1293;
37. b) Q.-Q. Yang, C. Xiao, L.-Q. Lu, J. An, F. Tan, B.-J. Li, W.-J. Xiao, Angew. Chem. 2012, 124, 9271-9274;
38. Angew. Chem. Int. Ed. 2012, 51, 9137-9140;
39. c) J. An, L.-Q. Lu, Q.-Q. Yang, T. Wang, W.-J. Xiao, Org. Lett. 2013, 15, 542-545;
40. d) Q.-Q. Yang, Q. Wang, J. An, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Chem. Eur. J. 2013, 19, 8401-8404;
41. e) H.-G. Cheng, L.-Q. Lu, T. Wang, Q.-Q. Yang, X.-P. Liu, Y. Li, Q.-H. Deng, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2013, 125, 3332-3336;
42. Angew. Chem. Int. Ed. 2013, 52, 3250-3254;
43. f) X.-Q. Hu, J.-R. Chen, S. Gao, B. Feng, L.-Q. Lu, W.-J. Xiao, Chem. Commun. 2013, 49, 7905-7907.
44. a) Y.-Q. Zou, L.-Q. Lu, L. Fu, N.-J. Chang, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2011, 123, 7309-7313;
45. Angew. Chem. Int. Ed. 2011, 50, 7171-7175;
46. b) J. Xuan, Y. Cheng, J. An, L.-Q. Lu, X.-X. Zhang, W.-J. Xiao, Chem. Commun. 2011, 47, 8337-8339;
47. c) Y.-Q. Zou, J.-R. Chen, X.-P. Liu, L.-Q. Lu, R. L. Davis, K. A. Jørgensen, W.-J. Xiao, Angew. Chem. 2012, 124, 808-812;
48. Angew. Chem. Int. Ed. 2012, 51, 784-788;
49. d) J. Xuan, Z.-J. Feng, S.-W. Duan, W.-J. Xiao, RSC Adv. 2012, 2, 4065-4068;
50. e) J. An, Y.-Q. Zou, Q.-Q. Yang, Q. Wang, W.-J. Xiao, Adv. Synth. Catal. 2013, 355, 1483-1489;
51. f) Y.-Q. Zou, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2013, 125, 11917-11919;
52. Angew. Chem. Int. Ed. 2013, 52, 11701-11703.
53. a) T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527-532;
54. b) J. M. Narayanam, C. R. Stephenson, Chem. Soc. Rev. 2011, 40, 102-113;
55. c) F. Teplý, Collect. Czech. Chem. Commun. 2011, 76, 859-917;
56. d) L. Shi, W. Xia, Chem. Soc. Rev. 2012, 41, 7687-7697;
57. e) S. Maity, N. Zheng, Synlett 2012, 23, 1851-1856;
58. f) J. Xuan, W.-J. Xiao, Angew. Chem. 2012, 124, 6934-6944;
59. Angew. Chem. Int. Ed. 2012, 51, 6828-6838;
60. g) C. K. Prier, D. A. Rankic, D. W. MacMillan, Chem. Rev. 2013, 113, 5322-5363;
61. h) D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97-113.
62. a) M. R. Heinrich, Chem. Eur. J. 2009, 15, 820-833;
63. b) D. P. Hari, B. König, Angew. Chem. 2013, 125, 4832-4842;
64. Angew. Chem. Int. Ed. 2013, 52, 4734-4743;
65. c) F. Mo, G. Dong, Y. Zhang, J. Wang, Org. Biomol. Chem. 2013, 11, 1582-1593.
66. a) D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18566-18569;
67. b) D. P. Hari, P. Schroll, B. König, J. Am. Chem. Soc. 2012, 134, 2958-2961;
68. c) P. Schroll, D. P. Hari, B. König, ChemistryOpen 2012, 1, 130-133;
69. d) J. Yu, L. Zhang, G. Yan, Adv. Synth. Catal. 2012, 354, 2625-2628;
70. e) B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc. 2013, 135, 5505-5508;
71. f) D. P. Hari, T. Hering, B. König, Angew. Chem. 2014, 126, 743-747;
72. Angew. Chem. Int. Ed. 2014, 53, 725-728.
73. a) S. R. Neufeldt, M. S. Sanford, Adv. Synth. Catal. 2012, 354, 3517-3522;
74. b) S. Donck, A. Baroudi, L. Fensterbank, J.-P. Goddard, C. Ollivier, Adv. Synth. Catal. 2013, 355, 1477-1482;
75. c) G. Fumagalli, S. Boyd, M. F. Greaney, Org. Lett. 2013, 15, 4398-4401.
76. R. M. Elofson, F. F. Gadallah, J. Org. Chem. 1969, 34, 854-857.
77. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
78. a) Y. Asakawa, K. Takikawa, M. Tori, Phytochemistry 1987, 26, 1023-1025;
79. b) R. S. Mali, K. N. Babu, P. G. Jagtap, J. Chem. Soc. Perkin Trans. 1 2001, 3017-3019.