π-acid mediated insertion of alkynes into carbon-heteroatom σ-bonds

Synthesis (Germany)

Volumn 44, Issue 22, 2012, Pages 3401-3420

  Adcock, Holly V ^a   Davies, Paul W ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

alkynes; catalysis; cyclisation; gold; heterocycles; nucleophilic addition; platinum

Indexed keywords

ACID CATALYSIS; ALKYLATING AGENTS; ALKYNES; ALKYNYLS; CARBON-HETEROATOM BONDS; HETEROATOMS; HETEROCYCLES; NATURAL PRODUCTS; NUCLEOPHILIC ADDITIONS; NUCLEOPHILIC ATTACK; OXIDATION LEVEL; OXONIUM; OXONIUM ION; SIGMATROPIC REARRANGEMENTS; TO EFFECT;

ADDITION REACTIONS; CARBON; CARBOXYLATION; CATALYSIS; CHEMICAL REACTIVITY; CYCLIZATION; GOLD; INTERNAL OXIDATION; PALLADIUM; PLATINUM;

ACETYLENE;

ALKYNE DERIVATIVE; ALKYNYL BENZOIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; CARBON; GOLD CHLORIDE; HYDRONIUM ION; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

AMINATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; CYCLIZATION; ELECTROPHILICITY; HYDROGEN BOND; HYDROLYSIS; HYDROXYLATION; ISOMERIZATION; NUCLEOPHILICITY; PROTON TRANSPORT; REVIEW; SIGMA BOND; STOICHIOMETRY; SYNTHESIS; TRANSESTERIFICATION;

EID: 84868627380     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316788     Document Type: Review

References (75)

1. Kang E. J., Lee E. Chem. Rev.: 2005; 105 4348
2. Saleem M., Kim H. J., Ali M. S., Lee Y. S. Nat. Prod. Rep.: 2005; 22 696
3. Kumar K., Waldmann H. Angew. Chem. Int. Ed.: 2009; 48 3224
4. Zhong J. Nat. Prod. Rep.: 2011; 28 1143
5. Nakamura I., Yamamoto Y. Chem. Rev.: 2004; 104 2127
6. Zeni G., Larock R. C. Chem. Rev.: 2004; 104 2285
7. Russel J. S., Pelkey E. T., Greger J. G. Prog. Heterocycl. Chem.: 2011; 23 155
8. Yeung K. S., Peng X. S., Wu J., Hou X. L. Prog. Heterocycl. Chem.: 2011; 23 195
9. Majumdar K. C., Samanta S., Sinha B. Synthesis: 2012; 812
10. Trost B. M. Science: 1991; 254 1471
11. Trost B. M. Angew. Chem. Int. Ed.: 1995; 34 259
12. Trost B. M. Acc. Chem. Res.: 2002; 35 695
13. Gaich T., Baran P. S. J. Org. Chem.: 2010; 75 4657
14. Wender P. A., Verma V. A., Paxton T. J., Pillow T. H. Acc. Chem. Res.: 2008; 41 40
15. Aubert C., Buisine O., Malacria M. Chem. Rev.: 2002; 102 813
16. Aubert C., Fensterbank P., Garcia P., Malacria M., Simonneau A. Chem. Rev.: 2011; 111 1954
17. Watson I. D. G, Toste F. D. Chem. Sci.: 2012; in press, DOI 10.1039/c2sc20542d
18. Severin R., Doye S. Chem. Soc. Rev.: 2007; 36 1407
19. Müller T. E., Hultzsch K. C., Miguel Y., Foubelo F., Tada M. Chem. Rev.: 2008; 108 3795
20. Pohlki F., Doye S. Chem. Soc. Rev.: 2003; 32 104
21. Fürstner A., Davies P. W. Angew. Chem. Int. Ed.: 2007; 46 3410
22. Hashmi A. S. K, Hutchings G. J. Angew. Chem. Int. Ed.: 2006; 45 7896
23. Fürstner A. Chem. Soc. Rev.: 2009; 38 3208
24. Gorin D. J., Toste F. D. Nature: 2007; 446 395
25. Li J., Brouwer C., He C. Chem. Rev.: 2008; 108 3239
26. Hashmi A. S. K. Angew. Chem. Int. Ed.: 2010; 49 5232
27. Jiménez-Núñez E., Echavarren A. M. Chem. Commun.: 2007; 333
28. Widenhoefer R. A., Han X. Eur. J. Org. Chem.: 2006; 4555
29. Shen H. C. Tetrahedron: 2008; 64 3885
30. Shen H. C. Tetrahedron: 2008; 64 7847
31. Kirsch S. F. Synthesis: 2008; 20 3183
32. Patil N. T., Yamamoto Y. Chem. Rev.: 2008; 108 3395
33. Hashmi A. S. K, Buehrle M. Aldrichimica Acta: 2010; 43 27
34. Huang H., Zhou Y., Liu H. Beilstein J. Org. Chem.: 2011; 7 897
35. Alcaide B., Almendros P., Alonso J. M. Org. Biomol. Chem.: 2011; 9 4405
36. Patil N. T., Singh V. J. Organomet. Chem.: 2011; 696 419
37. Corma A., Leyva-Pérez A., Sabater M. J. Chem. Rev.: 2011; 111 1657
38. For X→C functional group migrations in heterocycle synthesis, see: Patil N. T., Kavthe R. D., Yamamoto Y. Adv. Heterocycl. Chem.: 2010; 101 75
39. Brenzowich W. E. Jr. Angew. Chem. Int. Ed.: 2012; 51 8933
40. Crouter C. M., Hashmi A. S. K, Perpointner M. ChemCatChem: 2010; 2 1226
41. Liu B., De Brabander J. K. Org. Lett.: 2006; 8 4907
42. Li Y., Zhou F., Forsyth C. J. Angew. Chem. Int. Ed.: 2007; 46 279
43. Jung H. H., Floreancig P. E. J. Org. Chem.: 2007; 72 7359
44. Trost B. M., OBoyle B. M., Hund D. J. Am. Chem. Soc.: 2009; 131 15061
45. Fortner K. C., Kato D., Tanaka Y., Shair M. D. J. Am. Chem. Soc.: 2010; 132 275
46. Fang C., Pang Y., Forsyth C. J. Org. Lett.: 2010; 12 4528
47. Tlais S. F., Dudley G. B. Org. Lett.: 2010; 12 4698
48. Tlais S. F., Dudley G. B. J. Org. Chem.: 2011; 7 570
49. Benson S., Collin M.-P, Arlt A., Gabor B., Goddard R., Fürstner A. Angew. Chem. Int. Ed.: 2011; 50 8739
50. Chaładaj W., Corbet M., Fürstner A. Angew. Chem. Int. Ed.: 2012; 51 6929
51. Cariou K., Ronan B., Mignani S., Fensterbank L., Malacria M. Angew. Chem. Int. Ed.: 2007; 46 1881
52. For related gold-catalysed synthesis of 1-cyanoisoindoles, see: Heugebaert T. S. A, Stevens C. V. Org. Lett.: 2009; 11 5018
53. Ma S., Shi Z. J. Org. Chem.: 2003; 68 6149
54. Ma S., Shi Z. J. Org. Chem.: 1998; 63 6387
55. Cacchi S., Fabrizi G., Moro L. Tetrahedron Lett.: 1998; 39 5101
56. Cacchi S., Fabrizi G., Moro L. Synlett: 1998; 741
57. Montiero N., Balme G. Synlett: 1998; 746
58. Liu L.-P, Hammond G. B. Chem. Soc. Rev.: 2012; 41 3129
59. Egorova O. A., Seo H., Kim Y., Moon D., Rhee Y. M., Ahn K. H. Angew. Chem. Int. Ed.: 2011; 50 11446
60. Hashmi A. S. K, Ramamurthi T. D., Rominger F. Adv. Synth. Catal.: 2010; 352 971
61. Hashmi A. S. K, Schuster A. M., Rominger F. Angew. Chem. Int. Ed.: 2009; 48 8247
62. Liu L.-P, Hammond G. B. Chem.-Asian J.: 2009; 4 1230
63. Asao N., Aikawa H., Tago S., Umetsu K. Org. Lett.: 2007; 9 4299
64. Jean M., Renault J., Weghe P. V.-D, Asao N. Tetrahedron Lett.: 2010; 51 378
65. Aikawa H., Tago S., Umetsu K., Haginiwa N., Asao N. Tetrahedron: 2009; 65 1774
66. Crone B., Kirsch S. F. Chem.-Eur. J.: 2008; 14 3514
67. Dudnik A. S., Chernyak N., Gevorgyan V. Aldrichimica Acta: 2010; 43 37
68. Davies P. W., Martin N., Spencer N. Beilstein J. Org. Chem.: 2011; 7 839
69. Benedetti E., Lemiere G., Chapellet L.-L, Penoni A., Palmisano G., Malacria M., Goddard J.-P, Fensterbank L. Org. Lett.: 2010; 12 4396
70. Davies P. W., Martin N. Org. Lett.: 2009; 11 2293
71. Dudnik A. S., Sromek A. W., Rubina M., Kim J. T., Kelin A. V., Gevorgyan V. J. Am. Chem. Soc.: 2008; 130 1440
72. Dudnik A. S., Gevorgyan V. Angew. Chem. Int. Ed.: 2007; 46 5195
73. Gorin D. J., Davis N. R., Toste F. D. J. Am. Chem. Soc.: 2005; 127 11260
74. Keen N. T., Zaki A. I., Sims J. J. Phytochemistry: 1972; 11 1031
75. Morandi D., Le Quere J. L. New Phytol.: 1991; 117 75