Decarboxylative carbon-carbon bond-forming transformations of (hetero)aromatic carboxylic acids

Synthesis

Volumn 44, Issue 5, 2012, Pages 653-676

  Cornella, Josep ^a   Larrosa, Igor ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

carboxylic acids; catalysis; cross coupling; decarboxylation; palladium

Indexed keywords

AROMATIC CARBOXYLIC ACIDS; BOND FORMING; C-C BOND FORMING REACTION; CROSS-COUPLINGS; DECARBOXYLATION; HALOARENES; ORGANIC SYNTHESIS;

ACETYLENE; AROMATIC COMPOUNDS; CARBOXYLATION; CATALYSIS; COUPLINGS; OLEFINS; PALLADIUM;

CARBOXYLIC ACIDS;

1,3 OXAZOLE 4 CARBOXYLIC ACID; 1,3 THIAZOLE 4 CARBOXYLIC ACID; ACRYLIC ACID; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AROMATIC BENZOIC ACID DERIVATIVE; AROMATIC CARBOXYLIC ACID; AROMATIC CARBOXYLIC ACID DERIVATIVE; ARYL CHLORIDE DERIVATIVE; ARYL IODIDE DERIVATIVE; BENZOAZOLE DERIVATIVE; BENZOIC ACID; BROMINE DERIVATIVE; BROMOARENE DERIVATIVE; CARBON; CARBOXYLATE COPPER; COPPER ION; COUMARIN CARBOXYLIC ACID DERIVATIVE; DICYCLOHEXYL(2',4',6' TRIISOPROPYL[1,1' BIPHENYL] 2 YL)PHOSPHINE; GOLD; HETEROAROMATIC CARBOXYLIC ACID; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PSEUDOHALOARENE DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM; SILVER; STYRENE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CROSS COUPLING REACTION; DECARBOXYLATION; DECARBOXYLATIVE ARYLATION; DECARBOXYLATIVE CROSS COUPLING; DECARBOXYLATIVE HOMECOUPLING; DECARBOXYLATIVE SUZUKI CROSS COUPLING; ELECTROPHILICITY; OXIDATION; OXIDATIVE DECARBOXYLATIVE CROSS COUPLING; PROTODECARBOXYLATION; REVIEW; STOICHIOMETRY;

EID: 84857394510     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289686     Document Type: Review

References (88)

1. Other types of carboxylic acids have also been used in carbon-carbon bond-forming reactions (e.g., propargylic, aliphatic or 2-oxo carboxylic acids - see ref. 2), however this review will focus on the use of(hetero)aromatic carboxylic acids.
2. For other reviews on decarboxylative functionalization, see:, Satoh T, Miura M, Synthesis 2010 3395
3. Rodriguez N, Goossen L J., Chem. Soc. Rev. 2011 40 5030
4. Shang R, Liu L, Sci. China Chem. 2011 54 1670
5. Shepard A F., Winslow N R., Jonhson J R., J. Am. Chem. Soc. 1930 52 2083
6. Björklund C, Nilsson M, Acta Chem. Scand. 1968 22 2585
7. Chodowska-Palicka J, Nilsson M, Acta Chem. Scand. 1970 24 3353
8. Chodowska-Palicka J, Nilsson M, Acta Chem. Scand. 1971 25 3451
9. Cohen T, Schambach R A., J. Am. Chem. Soc. 1970 92 3189
10. Cohen T, Berninger R W., Wood J T., J. Org. Chem. 1978 43 837
11. Cairncross A, Roland J R., Henderson R M., Sheppard W A., J. Am. Chem. Soc. 1970 92 3187
12. Goossen L J., Thiel W R., Rodriguez N, Linder C, Melzer B, Adv. Synth. Catal. 2007 349 2241
13. Goossen L J., Manjolinho F, Khan B A., Rodriguez N, J. Org. Chem. 2009 74 2620
14. Tanaka D, Romeril S P., Myers A G., J. Am. Chem. Soc. 2005 127 10323
15. Dickstein J S., Mulrooney C A., OBrien E M., Morgan B J., Kozlowski M C., Org. Lett. 2007 9 2441
16. OBrien E M., Morgan B J., Kozlowski M C., Angew. Chem. Int. Ed. 2008 47 6877
17. NuñezMagro A A., Eastham G R., Cole-Hamilton D J., Dalton Trans. 2009 4683
18. Cornella J, Righi M, Larrosa I, Angew. Chem. Int. Ed. 2011 50 9429
19. Goossen L J., Linder C, Rodriguez N, Lange P P., Fromm A, Chem. Commun. 2009 7173
20. Cornella J, Sanchez C, Banawa D, Larrosa I, Chem. Commun. 2009 7176
21. Lu P, Sanchez C, Cornella J, Larrosa I, Org. Lett. 2009 11 5710
22. Jafarpour F, Jalalimanesh N, Olia M B. A., Kashani A O., Tetrahedron 2010 66 9508
23. Sun Z.-M, Zhang J, Zhao P, Org. Lett. 2010 12 992
24. Dupuy S, Lazreg F, Slawin A M. Z., Cazin C S. J., Nolan S P., Chem. Commun. 2011 47 5455
25. Cornella J, Rosillo-Lopez M, Larrosa I, Adv. Synth. Catal. 2011 353 1359
26. Similar conditions had previously been reported to mediate C-H activation processes in electron-deficient arenes:, Lu P, Boorman T C., Slawin A M. Z., Larrosa I, J. Am. Chem. Soc. 2010 132 5580
27. Nilsson M, Acta Chem. Scand. 1966 20 423
28. Nilsson M, Ullenius C, Acta Chem. Scand. 1968 22 1998
29. Heim A, Terpin A, Steglich W, Angew. Chem. Int. Ed. 1997 36 155
30. Peschko C, Winklhofer C, Steglich W, Chem. Eur. J. 2000 6 1147
31. Goossen L J., Deng G, Levy L M., Science 2006 313 662
32. Goossen L J., Rodriguez N, Melzer B, Linder C, Deng G, Levy L, J. Am. Chem. Soc. 2007 129 4824
33. Goossen L J., Zimmermann B, Linder C, Rodriguez N, Lange P P., Hartung J, Adv. Synth. Catal. 2009 351 2667
34. Goossen L J., Zimmermann B, Knauber T, Angew. Chem. Int. Ed. 2008 47 7103
35. Goossen L J., Rodriguez N, Linder C, J. Am. Chem. Soc. 2008 130 15248
36. Lange P P., Goossen L J., Podmore P, Underwood T, Sciammetta N, Chem. Commun. 2011 3628
37. Goossen L J., Rodriguez N, Lange P P., Linder C, Angew. Chem. Int. Ed. 2010 49 1111
38. Becht J.-M, Catala C, LeDrian C, Wagner A, Org. Lett. 2007 9 1781
39. Wang Z, Ding Q, He X, Wu J, Tetrahedron 2009 65 4635
40. Becht J.-M, LeDrian C, Org. Lett. 2008 10 3161
41. Zhang F, Greaney M F., Org. Lett. 2010 12 4745
42. Goossen L J., Lange P P., Rodriguez N, Linder C, Chem. Eur. J. 2010 16 3906
43. Forgione P, Brochu M.-C, St-Onge M, Thesen K H., Bailey M D., Bilodeau F, J. Am. Chem. Soc. 2006 128 11350
44. Bilodeau F, Brochu M.-C, Guimond N, Thesen K H., Forgione P, J. Org. Chem. 2010 75 1550
45. Nakano M, Tsurugi H, Satoh T, Miura M, Org. Lett. 2008 10 1851
46. Miyasaka M, Hirano K, Satoh T, Miura M, Adv. Synth. Catal. 2009 351 2683
47. Miyasaka M, Fukushima A, Satoh T, Hirano K, Miura M, Chem. Eur. J. 2009 15 3674
48. Shang R, Xu Q, Jiang Y.-Y, Wang Y, Liu L, Org. Lett. 2010 12 1000
49. Arroyave F A., Reynolds J R., Org. Lett. 2010 12 1328
50. Shang R, Fu Y, Wang Y, Xu Q, Yu H.-Z, Liu L, Angew. Chem. Int. Ed. 2009 48 9350
51. Shi W, Liu C, Lei A, Chem. Soc. Rev. 2011 40 2761
52. Dai J.-J, Liu J.-H, Luo D.-F, Liu L, Chem. Commun. 2011 47 677
53. Cornella J, Lahlali H, Larrosa I, Chem. Commun. 2010 46 8276
54. Voutchokva A, Coplin A, Leadbeater N E., Crabtree R H., Chem. Commun. 2008 6312
55. Wang C, Piel I, Glorius F, J. Am. Chem. Soc. 2009 131 4194
56. Cornella J, Lu P, Larrosa I, Org. Lett. 2009 11 5506
57. Stuart D R., Fagnou K, Science 2007 316 1172
58. Stuart D R., Villemure E, Fagnou K, J. Am. Chem. Soc. 2007 129 12072
59. Lebrasseur N, Larrosa I, J. Am. Chem. Soc. 2008 130 2926
60. Phipps R J., Grimster N P., Gaunt M J., J. Am. Chem. Soc. 2008 130 8172
61. Yang S.-D, Sun C.-L, Fang Z, Li B.-J, Li Y.-Z, Shi Z.-J, Angew. Chem. Int. Ed. 2008 47 1473
62. Joucla L, Batail N, Djackovitch L, Adv. Synth. Catal. 2010 352 2929
63. Zunjun L, Bangben Y, Yuhong Z, Org. Lett. 2010 12 3185
64. Liang W, Wen-Bin Y, Cun C, Chem. Commun. 2011 47 806
65. Nadres E T., Lazareva A, Daugulis O, J. Org. Chem. 2011 76 471
66. Joucla L, Djackovitch L, Adv. Synth. Catal. 2009 351 673
67. Bellina F, Rossi R, Tetrahedron 2009 65 10269
68. Zhou J, Hu P, Zhang M, Huang S, Wang M, Su W, Chem. Eur. J. 2010 16 5876
69. Zhang F, Greaney M F., Angew. Chem. Int. Ed. 2010 49 2768
70. Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo C.-C, Org. Lett. 2010 12 1564
71. Zhao H, Wei Y, Xu J, Kan J, Su W, Hong M, J. Org. Chem. 2011 76 882
72. Yu W.-Y, Sit W N., Zhou Z, Chan A S.-C, Org. Lett. 2009 11 3174
73. Myers A G., Tanaka D, Mannion M R., J. Am. Chem. Soc. 2002 124 11250
74. Tanaka D, Myers A G., Org. Lett. 2004 6 433
75. Hu P, Kan J, Su W, Hong M, Org. Lett. 2009 11 2341
76. Fu Z, Huang S, Su W, Hong M, Org. Lett. 2010 12 4992
77. Fu Z, Huang S, Kan J, Su W, Hong M, Dalton Trans. 2010 39 11317
78. Zhao Y, Zhang Y, Wang J, Li H, Wu L, Liu Z, Synlett 2010 2352
79. Wang J, Cui Z, Zhang Y, Li H, Wu L.-M, Liu Z, Org. Biomol. Chem. 2011 9 663
80. Goossen L J., Zimmermann B, Knauber T, Beilstein J. Org. Chem. 2010 6 43
81. Ueaura K, Satoh T, Miura M, J. Org. Chem. 2007 72 5362
82. Shimizu M, Hirano K, Satoh T, Miura M, J. Org. Chem. 2009 74 3478
83. Yamashita M, Hirano K, Satoh T, Miura M, Org. Lett. 2009 11 2337
84. Wang C, Rakshit S, Glorius F, J. Am. Chem. Soc. 2010 132 14006
85. Huang X.-C, Wang F, Liang Y, Li J.-H, Org. Lett. 2009 11 1139
86. Zhang M, Zhou J, Kan J, Wang M, Su W, Hong M, Chem. Commun. 2011 46 5455
87. Luo Y, Wu J, Chem. Commun. 2010 46 3785
88. Lindh J, Sjörberg P J., Larhed M, Angew. Chem. Int. Ed. 2010 49 7733