Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri- and Tetrasubstituted Cyclobutanes

Angewandte Chemie - International Edition

Volumn 55, Issue 15, 2016, Pages 4748-4752

  Colomer, Ignacio ^a   Coura Barcelos, Rosimeire ^a   Donohoe, Timothy J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

cyclizations; dimerization; hypervalent compounds; small ring systems; total synthesis

Indexed keywords

CHEMICAL REACTIONS; DIMERIZATION; IODINE; STYRENE;

CYCLIZATIONS; DESS-MARTIN PERIODINANE; HYPERVALENT COMPOUNDS; HYPERVALENT IODINE REAGENTS; MILD REACTION CONDITIONS; SMALL RING SYSTEMS; STEREOSELECTIVE FORMATION; TOTAL SYNTHESIS;

TRICHLOROETHYLENE;

EID: 84960193678     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511683     Document Type: Article

References (62)

1. V. V. Zhdankin, Hypervalent Iodine Chemistry, Wiley, Hoboken, 2013;
2. V. V. Zhdankin, J. Org. Chem. 2011, 76, 1185;
3. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073. For a general perspective of iodine chemistry, see
4. F. C. Küpper, M. C. Feiters, B. Olofsson, T. Kaiho, S. Yanagida, M. B. Zimmermann, L. J. Carpenter, G. W. Luther, Z. Lu, M. Jonsson, L. Kloo, Angew. Chem. Int. Ed. 2011, 50, 11598;
5. Angew. Chem. 2011, 123, 11802.
6. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. Int. Ed. 2000, 39, 2525;
7. Angew. Chem. 2000, 112, 2625;
8. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, S. Barluenga, K. W. Hunt, R. Kranich, J. A. Vega, J. Am. Chem. Soc. 2002, 124, 2233;
9. B. Janza, A. Studer, J. Org. Chem. 2005, 70, 6991;
10. K. C. Nicolaou, P. S. Baran, R. Kranich, Y.-L. Zhong, K. Sugita, N. Zou, Angew. Chem. Int. Ed. 2001, 40, 202;
11. 2 under elevated temperatures or under irradiation has been used in radical pathways to generate oxygen or nitrogen radicals, such as the Suárez reaction
12. J. I. Concepción, C. G. Francisco, R. Hernández, J. A. Salazar, E. Suárez, Tetrahedron Lett. 1984, 25, 1953;
13. C. Francisco, C. C. González, E. Suárez, Tetrahedron Lett. 1997, 38, 4141;
14. A. Boto, R. Hernández, E. Suárez, Tetrahedron Lett. 2000, 41, 2899;
15. A. Boto, R. Hernández, Y. de León, E. Suárez, Tetrahedron Lett. 2001, 66, 7796;
16. D. Alvarez-Dorta, E. I. León, A. R. Kennedy, A. Martín, I. Pérez-Martín, E. Suárez, Angew. Chem. Int. Ed. 2015, 54, 3674;
17. Angew. Chem. 2015, 127, 3745. For a review see
18. H. Togo, M. Katohgi, Synlett 2001, 565, and references therein.
19. Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, T. Yakura, Tetrahedron Lett. 1991, 32, 4321;
20. Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684;
21. H. Hamamoto, K. Hata, H. Nambu, Y. Shiozaki, H. Tohma, Y. Kita, Tetrahedron Lett. 2004, 45, 2293;
22. T. Dohi, M. Ito, N. Yamaoka, K. Morimoto, H. Fujioka, Y. Kita, Angew. Chem. Int. Ed. 2010, 49, 3334;
23. Angew. Chem. 2010, 122, 3406.
24. Y. Xu, M. L. Conner, M. K. Brown, Angew. Chem. Int. Ed. 2015, 54, 11918;
25. Angew. Chem. 2015, 127, 12086. For an update of thermal cyclobutane formation, see
26. B. Alcaide, C. Aragoncillo, P. Almendros, in Comprehensive Organic Synthesis II, 2 nd ed., (Ed.: P. Knochel,), Elsevier, Amsterdam, 2014, pp. 66-84. For [2+2] photocycloaddition using α,β-unsaturated ketones, see
27. P. Margaretha, Helv. Chim. Acta 2014, 97, 1027. For the stereocontrolled synthesis of cyclobutanones, see
28. F. Secci, A. Frongia, P. Piras, Molecules 2013, 18, 15541. For the use of cyclobutanes in catalysis, see
29. T. Seiser, T. Saget, D. N. Tran, N. Cramer, Angew. Chem. Int. Ed. 2011, 50, 7740;
30. Angew. Chem. 2011, 123, 7884. For allenes in [2+2] cycloaddition, see
31. B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783.
32. J. M. Hoyt, V. A. Schmidt, A. M. Tondreau, P. J. Chirik, Science 2015, 349, 960. Copper-catalyzed boration and cyclization of homoallylic sulfonates
33. H. Ito, T. Toyoda, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 5990. Extensive work has been done on the metal-catalyzed intramolecular [2+2] of allenes. For nickel, see
34. N. N. Noucti, E. J. Alexanian, Angew. Chem. Int. Ed. 2015, 54, 5447;
35. Angew. Chem. 2015, 127, 5537. For ruthenium, see
36. M. Gulías, A. Collado, B. Trillo, F. López, E. Oñate, M. A. Esteruelas, J. L. Mascareñas, J. Am. Chem. Soc. 2011, 133, 7660. For gold see
37. M. R. Luzung, P. Mauleón, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12402.
38. A. Ledwith, Acc. Chem. Res. 1972, 5, 133;
39. F. A. Bell, R. A. Crellin, H. Fujii, A. Ledwith, J. Chem. Soc. D 1969, 251.
40. N. L. Bauld, D. J. Bellville, B. Harirchian, K. T. Lorenz, R. A. Pabon, D. W. Reynolds, D. D. Wirth, H. S. Chiou, B. K. Marsh, Acc. Chem. Res. 1987, 20, 371;
41. N. L. Bauld, D. J. Bellville, R. Pabon, R. Chelsky, G. Green, J. Am. Chem. Soc. 1983, 105, 2378;
42. N. L. Bauld, R. Pabon, J. Am. Chem. Soc. 1983, 105, 633.
43. A radical cation intermediate has been detected using extractive electrospray ionization mass spectrometry (EESI-MS). See:, C. A. Marquez, H. Wang, F. Fabbretti, J. O. Metzger, J. Am. Chem. Soc. 2008, 130, 17208.
44. M. A. Ischay, Z. Lu, T. P. Yoon, J. Am. Chem. Soc. 2010, 132, 8572. For cross-dimerization of styrenes leading to trisubstitued cyclobutanes using ruthenium-based photoredox, see
45. M. A. Ischay, M. S. Ament, T. P. Yoon, Chem. Sci. 2012, 3, 2807.
46. For homodimerization of styrenes using a combination of organic photoredox catalyst and electron relay, see:, M. Riener, D. A. Nicewicz, Chem. Sci. 2013, 4, 2625.
47. V. M. Dembitsky, Phytomedicine 2014, 21, 1559;
48. A. Sergeiko, V. V. Poroikov, L. O. Hanuš, V. M. Dembitsky, Open Med. Chem. J. 2008, 2, 26;
49. V. Dembitsky, J. Nat. Med. 2008, 62, 1.
50. K. Wei, W. Li, K. Koike, Y. Chen, T. Nikaido, J. Org. Chem. 2005, 70, 1164. Nigramide R has also been isolated recently from Piper retrofractum
51. R. Muharini, Z. Liu, W. Lin, P. Proksch, Tetrahedron Lett. 2015, 56, 2521. For other members isolated from the genus Piper, see
52. S. Tsukamoto, B.-C. Cha, T. Ohta, Tetrahedron 2002, 58, 1667;
53. S. Tsukamoto, K. Tomise, K. Miyakawa, B.-C. Cha, T. Abe, T. Hamada, H. Hirota, T. Ohta, Bioorg. Med. Chem. 2002, 10, 2981.
54. Y. Tian, X. Xu, L. Zhang, J. Qu, Org. Lett. 2015, 18, 268, and references therein. Alternatively, and based on DFT studies, HFIP has been proposed to stabilize a charged transition state through hydrogen-bonding interactions
55. M. C. DiPoto, R. P. Hughes, J. Wu, J. Am. Chem. Soc. 2015, 137, 14861.
56. Y.-M. Wang, N. C. Bruno, Á. L. Placeres, S. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 10524;
57. J. Du, K. L. Skubi, D. M. Schultz, T. P. Yoon, Science 2014, 344, 392;
58. C. Müller, A. Bauer, M. M. Maturi, M. C. Cuquerella, M. A. Miranda, T. Bach, J. Am. Chem. Soc. 2011, 133, 16689;
59. S. C. Coote, T. Bach, J. Am. Chem. Soc. 2013, 135, 14948;
60. Ł. Albrecht, G. Dickmeiss, F. C. Acosta, C. Rodríguez-Escrich, R. L. Davis, K. A. Jørgensen, J. Am. Chem. Soc. 2012, 134, 2543.
61. For the inhibitory activity study of nigramide R, see:, Subehan, T. Usia, S. Kadota, Y. Tezuka, Planta Med. 2006, 72, 527.
62. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936.