Silver-mediated alkyne annulations by C-H/P-H functionalizations: Step-economical access to benzophospholes

Synthesis (Germany)

Volumn 46, Issue 17, 2014, Pages 2297-2304

  Ma, Wenbo ^a   Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

alkynes; annulation; phosphinate; phosphine oxide; silver

Indexed keywords

HYDROCARBONS; PHOSPHORUS COMPOUNDS;

ALKYNES; ANNULATION; FUNCTIONALIZATIONS; PHOSPHINATE; PHOSPHINE OXIDE; PHOSPHOLES; SECONDARY PHOSPHINES;

SILVER;

1 (TERT BUTYL) 2,3 DIPHENYL 1H PHOSPHINDOLE 1 OXIDE; 1 CYCLOHEXYL 2,3 DIPHENYLPHOSPHINDOLE 1 OXIDE; 1 ETHOXY 2,3 BIS(4 FLUOROPHENYL)PHOSPHINDOLE 1 OXIDE; 1 ETHOXY 2,3 DIPHENYLPHOSPHINDOLE 1 OXIDE; 1 ISOPROPYL 2,3 DIPHENYL 1H PHOSPHINDOLE 1 OXIDE; 1 METHYL 2,3 DIPHENYL 1H PHOSPHINDOLE 1 OXIDE; 1 PHENYL 2,3 DIPROPYL 1H PHOSPHINDOLE 1 OXIDE; 1,2,3 TRIPHENYLPHOSPHINDOLE 1 OXIDE; 2 BUTYL 1,3 DIPHENYLPHOSPHINDOLE 1 OXIDE; 2 CYCLOPROPYL 1,3 DIPHENYLPHOSPHINDOLE 1 OXIDE; 2 METHYL 1,3 DIPHENYLPHOSPHINDOLE 1 OXIDE; 2,3 BIS(4 CHLOROPHENYL) 1 ETHOXY 1H PHOSPHINDOLE 1 OXIDE; 2,3 BIS(4 CHLOROPHENYL) 1 PHENYL 1H PHOSPHINDOLE 1 OXIDE; 4 METHYL 2,3 DIPHENYL 1 (2 TOLYL)PHOSPHINDOLE 1 OXIDE; 6 ETHOXY 4,5 DIPHENYLPHOSPHOLO[2,3 B]THIOPHENE 6 OXIDE; 7 METHYL 2,3 DIPHENYL 1 (2 TOLYL)PHOSPHINDOLE 1 OXIDE; ALKYNE; BENZO[B]PHOSPHOLE OXIDE; ETHOXY 2,3 BIS[4 (TRIFLUOROMETHYL)PHENYL] 1H PHOSPHINDOLE 1 OXIDE; OXIDE; RUTHENIUM COMPLEX; SILVER; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; C H FUNCTIONALIZATION; CATALYSIS; CHEMICAL BOND; CHEMICAL PARAMETERS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CONTROLLED STUDY; P H FUNCTIONALIZATION; REGIOSELECTIVITY; SYNTHESIS;

EID: 84906781171     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338630     Document Type: Article

References (58)

1. Stolar M., Baumgartner T.; Chem. Asian J.; 2014, 9: in press; DOI: 10.1002/asia.201301670. For selected examples, see
2. He X., Woo A. Y. Y, Borau-Garcia J., Baumgartner T. Chem. Eur. J.: 2013; 19 7620
3. Ren Y., Baumgartner T. J. Am. Chem. Soc.: 2011; 133 1328
4. Matano Y., Saito A., Fukushima T., Tokudome Y., Suzuki F., Sakamaki D., Kaji H., Ito A., Tanaka K., Imahori H. Angew. Chem. Int. Ed.: 2011; 50 8016
5. Ren Y., Kan W. H., Henderson M. A., Bomben P. G., Berlinguette C. P., Thangadurai V., Baumgartner T. J. Am. Chem. Soc.: 2011; 133 17014
6. Sanji T., Shiraishi K., Tanaka M. Org. Lett.: 2007; 9 3611
7. Lampin J.-P, Mathey F. J. Organomet. Chem.: 1974; 71 239
8. Hayashi Y., Matano Y., Suda K., Kimura Y., Nakao Y., Imahori K. Chem. Eur. J.: 2012; 18 15972
9. Fukazawa A., Ichihashi Y., Kosaka Y., Yamaguchi S. Chem. Asian J.: 2009; 4 1729
10. Tsuji H., Sato K., Ilies L., Itoh Y., Sato Y., Nakamura E. Org. Lett.: 2008; 10 2263
11. Sanji T., Shiraishi K., Kashiwabara T., Tanaka M. Org. Lett.: 2008; 10 2689
12. Märkl G., Jin G. Y., Berr K.-P. Tetrahedron Lett.: 1993; 34 3103
13. Balthazor T. M. J. Org. Chem.: 1980; 45 2519
14. Wender P. A. Tetrahedron: 2013; 69 7529
15. Trost B. M. Acc. Chem. Res.: 2002; 35 695
16. Girard S. A., Knauber T., Li C. J. Angew. Chem. Int. Ed.: 2014; 53 74
17. Thirunavukkarasu V. S., Kozhushkov S. I., Ackermann L. Chem. Commun.: 2014; 50 29
18. Colby D. A., Tsai A. S., Bergman R. G., Ellman J. A. Acc. Chem. Res.: 2012; 45 814
19. Yamaguchi J., Yamaguchi A. D., Itami K. Angew. Chem. Int. Ed.: 2012; 51 8960
20. Cho S. H., Kim J. Y., Kwak J., Chang S. Chem. Soc. Rev.: 2011; 40 5068
21. Ackermann L. Chem. Rev.: 2011; 111 1315
22. Wencel-Delord J., Dröge T., Liu F., Glorius F. Chem. Soc. Rev.: 2011; 40 4740
23. Ackermann L. Acc. Chem. Res.: 2014; 47 281
24. Arockiam P., Bruneau C., Dixneuf P. H. Chem. Rev.: 2012; 112 5879
25. Song G., Wang F., Li X. Chem. Soc. Rev.: 2012; 41 3651
26. Satoh T., Miura M. Chem. Eur. J.: 2010; 16 11212; and references cited therein
27. Song W., Ackermann L. Chem. Commun.: 2013; 49 6638
28. Baba K., Tobisu M., Chatani N. Angew. Chem. Int. Ed.: 2013; 53 11892
29. Wang H., Grohmann C., Nimphius C., Glorius F. J. Am. Chem. Soc.: 2012; 134 19592
30. Ma W., Graczyk K., Ackermann L. Org. Lett.: 2012; 14 6318
31. Morimoto K., Hirano K., Satoh T., Miura M. J. Org. Chem.: 2011; 76 9548
32. Huestis M. P., Chan L. N., Stuart D. R., Fagnou K. Angew. Chem. Int. Ed.: 2011; 50 11338
33. Shiota H., Ano Y., Aihara Y., Fukumoto Y., Chatani N. J. Am. Chem. Soc.: 2011; 133 14952
34. Chen J., Song G., Pan C.-L, Li X. Org. Lett.: 2010; 12 5426
35. Stuart D. R., Bertrand-Laperle M., Burgess K. M. N, Fagnou K. J. Am. Chem. Soc.: 2008; 130 16474
36. Ueura K., Satoh T., Miura M. Org. Lett.: 2007; 9 1407
37. Park Y., Seo J., Park S., Yoo E. J., Lee P. H. Chem. Eur. J.: 2013; 19 16461
38. Zhao D. C., Nimphius C., Lindale M., Glorius F. Org. Lett.: 2013; 15 4504
39. Ryu T., Kim J., Park Y., Kim S., Lee P. H. Org. Lett.: 2013; 15 3986
40. Seo J., Park Y., Jeon I., Ryu T., Park S., Lee P. H. Org. Lett.: 2013; 15 3358
41. Park S., Seo B., Shin S., Son J.-Y, Lee P. H. Chem. Commun.: 2013; 49 8671
42. Unoh Y., Hashimoto Y., Takeda D., Hirano K., Satoh T., Miura M. Org. Lett.: 2013; 15 3258
43. Itoh M., Hashimoto Y., Hirano K., Satoh T., Miura M. J. Org. Chem.: 2013; 78 8098
44. Kuninobu Y., Yoshida T., Takai K. J. Org. Chem.: 2011; 76 7370
45. Ackermann L., Barfüsser S., Kornhaass C., Kapdi A. R. Org. Lett.: 2011; 13 3082
46. Ackermann L., Kapdi A. R., Fenner S., Kornhaa C., Schulzke C. Chem. Eur. J.: 2011; 17 2965
47. Ackermann L., Born R., Spatz J. H., Meyer D. Angew. Chem. Int. Ed.: 2005; 44 7216
48. Ackermann L. Org. Lett.: 2005; 7 3123
49. Ackermann L., Born R. Angew. Chem. Int. Ed.: 2005; 44 2444
50. Ackermann L. Isr. J. Chem.: 2010; 50 652
51. Ackermann L. Synthesis: 2006; 1557
52. He C., Guo S., Ke J., Hao J., Xu H., Chen H., Lei A. J. Am. Chem. Soc.: 2012; 134 5766
53. He C., Hao J., Xu H., Mo Y., Liu H., Han J., Lei A. Chem. Commun.: 2012; 48 11073
54. Chen Y., Duan W. J. Am. Chem. Soc.: 2013; 135 16754
55. Unoh Y., Hirano K., Satoh T., Miura M. Angew. Chem. Int. Ed.: 2013; 52 12975
56. Li Y.-M, Sun M., Wang H.-L, Tian Q.-P, Yang S.-D. Angew. Chem. Int. Ed.: 2013; 52 3972
57. Bowman W. R., Storey J. M. D. Chem. Soc. Rev.: 2007; 36 1803
58. Studer A., Bossart M. Tetrahedron: 2001; 57 9649