Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts

Organic Letters

Volumn 13, Issue 13, 2011, Pages 3462-3465

  Petersen, Tue B ^a   Khan, Rehan ^a   Olofsson, Berit ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBOXYLIC ACID; CATION; ESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANIONS; CARBOXYLIC ACIDS; ESTERS; MOLECULAR STRUCTURE; ONIUM COMPOUNDS;

EID: 79959716327     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2012082     Document Type: Article

References (56)

1. Otera, J. Chem. Rev. 1993, 93, 1449-1470
2. Otera, J.; Nishikido, J. Esterification, 2 nd ed.; Wiley-VCH: Weinheim, 2009.
3. Vorbrüggen, H. Synlett 2008, 1603-1617
4. Aelony, D. J. Am. Oil Chem. Soc. 1955, 32, 170-172
5. Offenhauer, R. D. J. Chem. Educ. 1964, 41, 39
6. Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140-1142
7. Ishihara, K. Tetrahedron 2009, 65, 1085-1109
8. Parish, R. C.; Stock, L. M. Tetrahedron Lett. 1964, 1285-1288
9. Kim, S.; Lee, W. J.; Lee, J. I. Bull. Korean Chem. Soc. 1984, 5, 187-190
10. Hosseini Sarvari, M.; Sharghi, H. Tetrahedron 2005, 61, 10903-10907
11. Chakraborti, A. K.; Shivani J. Org. Chem. 2006, 71, 5785-5788
12. Neises, B.; Steglich, W. Angew. Chem. Int. Ed. Engl. 1978, 17, 522-524 Mitsunobu reactions: Fitzjarrald, V. P.; Pongdee, R. Tetrahedron Lett. 2007, 48, 3553-3557
13. Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Motevalli, S. J. Org. Chem. 2008, 73, 4882-4887
14. Zhang, L.; Zhang, G.; Zhang, M.; Cheng, J. J. Org. Chem. 2010, 75, 7472-7474
15. Luo, F.; Pan, C.; Qian, P.; Cheng, J. Synthesis 2010, 2005-2010
16. Kim, S.; Lee, J. I. J. Org. Chem. 1984, 49, 1712-1716
17. For a Cu-catalyzed coupling of an aryl halide with a carboxylic acid, see: Thasana, N.; Worayuthakarn, R.; Kradanrat, P.; Hohn, E.; Young, L.; Ruchirawat, S. J. Org. Chem. 2007, 72, 9379-9382
18. Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Mol. Catal. A: Chem. 1996, 111, 25-31
19. Watson, D. A.; Fan, X.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7096-7101
20. Wu, X.-F.; Neumann, H.; Beller, M. ChemCatChem 2010, 2, 509-513
21. For a coupling with diaryliodonium salts, see: Kang, S.-K.; Yamaguchi, T.; Ho, P.-S.; Kim, W.-Y.; Ryu, H.-C. J. Chem. Soc., Perkin Trans. 1 1998, 841-842
22. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169 For selected examples with hypervalent iodine, see: Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149-4152
23. Gou, F.-R.; Wang, X.-C.; Huo, P.-F.; Bi, H.-P.; Guan, Z.-H.; Liang, Y.-M. Org. Lett. 2009, 11, 5726-5729
24. Chernyak, N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270-8272
25. Qin, C.; Wu, H.; Chen, J.; Liu, M.; Cheng, J.; Su, W.; Ding, J. Org. Lett. 2008, 10, 1537-1540
26. Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P. M. P. Org. Lett. 2010, 12, 2686-2689
27. For a review, see: Merritt, E. A.; Olofsson, B. Synthesis 2011, 517-538 For catalytic systems (no aryl esters), see: Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244-12245
28. Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193-6196
29. Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem. Int. Ed. 2011, 50, 5331 - 5334.
30. Beringer, F. M.; Brierley, A.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. J. Am. Chem. Soc. 1953, 75, 2708-2712 (arylation of sodium benzoate, 5 equiv, with three different salts in 40-85% yield)
31. Nesmeyanov, A. N.; Makarova, L. G.; Tolstaya, T. P. Tetrahedron 1957, 1, 145-157 (no details given)
32. Fuson, R. C.; Albright, R. L. J. Am. Chem. Soc. 1959, 81, 487-490 (Cu-catalyzed synthesis of 2-acetoxy-2′-iodobiphenyl)
33. Xue, J.; Huang, X. Synth. Commun. 2007, 37, 2179-2185 For the use of other aryne precursors in esterification, see: Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 99-102
34. Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198-3209
35. Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610-2618
36. Bielawski, M.; Aili, D.; Olofsson, B. J. Org. Chem. 2008, 73, 4602-4607
37. Zhu, M.; Jalalian, N.; Olofsson, B. Synlett 2008, 592-596
38. Merritt, E. A.; Malmgren, J.; Klinke, F. J.; Olofsson, B. Synlett 2009, 2277-2280
39. Hossain, M. D.; Ikegami, Y.; Kitamura, T. J. Org. Chem. 2006, 71, 9903-9905
40. Hossain, M. D.; Kitamura, T. Bull. Chem. Soc. Jpn. 2007, 80, 2213-2219
41. For a review, see: Merritt, E. A.; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052-9070
42. Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M. J. Angew. Chem. Int. Ed. 2011, 50, 458-462
43. Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem. Int. Ed. 2011, 50, 463-466
44. Wagner, A. M.; Sanford, M. S. Org. Lett. 2011, 13, 288-291
45. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260-4263
46. Xiao, B.; Fu, Y.; Xu, J.; Gong, T.-J.; Dai, J.-J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468-469
47. Kita, Y.; Morimoto, K.; Ito, M.; Ogawa, C.; Goto, A.; Dohi, T. J. Am. Chem. Soc. 2009, 131, 1668-1669
48. Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Angew. Chem. Int. Ed. 2010, 49, 3334-3337
49. Morimoto, K.; Yamaoka, N.; Ogawa, C.; Nakae, T.; Fujioka, H.; Dohi, T.; Kita, Y. Org. Lett. 2010, 12, 3804-3807
50. Ackermann, L.; Dell'Acqua, M.; Fenner, S.; Vicente, R.; Sandmann, R. Org. Lett. 2011, 13, 2358-2360
51. Norrby, P.-O.; Petersen, T. B.; Bielawski, M.; Olofsson, B. Chem.-Eur. J. 2010, 16, 8251-8254
52. Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552-1555
53. Carroll, M. A.; Wood, R. A. Tetrahedron 2007, 63, 11349-11354
54. Racemic N -Boc-phenylglycine was used. Arylation of enantiomerically enriched carboxylic acids will be investigated for the full paper.
55. Oh, C. H.; Kim, J. S.; Jung, H. H. J. Org. Chem. 1999, 64, 1338-1340
56. This so called ortho -effect varies with the nucleophile and is sometimes overriden by electronic properties, so that aryl groups with electron-donating ortho -substituents are not transferred; see refs 17 and 19 and: Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. J. Am. Chem. Soc. 1999, 121, 9233-9234