Decarbonylative organoboron cross-coupling of esters by nickel catalysis

Nature Communications

Volumn 6, Issue , 2015, Pages

  Muto, Kei ^a   Yamaguchi, Junichiro ^b   Musaev, Djamaladdin G ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CARBOXYLIC ACID; AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; ESTER; HALIDE; NICKEL; ORGANOBORON DERIVATIVE; PHENYL GROUP;

AGROCHEMICAL; BORON; CARBOXYLIC ACID; CATALYSIS; CATALYST; CHEMISTRY; COUPLING; DRUG; ESTER; MOLECULAR ANALYSIS; NICKEL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; DECARBONYLATION; ELECTROPHILICITY; OXIDATIVE COUPLING; SUZUKI REACTION; THEORETICAL MODEL;

EID: 84934325537     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms8508     Document Type: Article

References (43)

1. Cross-Coupling Reactions: A Practical Guide. (ed. Miyaura, N.) vol. 219 (Springer, 2002)
2. Miyaura, N. & Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457-2483 (1995)
3. Lee, J. C. H. & Hall, D. G. Metal-Catalyzed Cross-Coupling Reactions and More. (eds de Meijere, A., Brase, S. & Oestreich, M.) 65-132 (Wiley-VCH, 2014)
4. Roglans, A., Pla-Quintana, A. & Moreno-Manas, M. Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions. Chem. Rev. 106, 4622-4643 (2006)
5. Blakey, S. B. & MacMillan, D. W. C. The first Suzuki cross-couplings of aryltrimethylammonium salts. J. Am. Chem. Soc. 125, 6046-6047 (2003)
6. Rosen, B. M. et al. Nickel-catalyzed cross-couplings involving carbonoxygen bonds. Chem. Rev. 111, 1346-1416 (2011)
7. Modha, S. G., Mehta, V. P. & Van der Eycken, E. V. Transition metal-catalyzed C-C bond formation via C-S bond cleavage: an overview. Chem. Soc. Rev. 42, 5042-5055 (2013)
8. Yu, D.-G. et al. Carbon-carbon formation via Ni-catalyzed Suzuki-Miyaura coupling through C-CN bond cleavage of aryl nitrile. Org. Lett. 11, 3374-3377 (2009)
9. Chen, X., Engle, K. M., Wang, D.-H. & Yu, J.-Q. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew. Chem. Int. Ed. 48, 5094-5115 (2009)
10. Sun, C.-L., Li, B.-J. & Shi, Z.-J. Pd-catalyzed oxidative coupling with organometallic reagents via C-H activation. Chem. Commun. 46, 677-685 (2010)
11. Yamaguchi, J. & Itami, K. in Metal-Catalyzed Cross-Coupling Reactions and More. (eds de Meijere, A., Brase, S. & Oestreich, M.) 1315-1387 (Wiley-VCH, 2014)
12. Mkhalid, I. A. I., Barnard, J. H., Marder, T. B., Murphy, J. M. & Hartwig, J. F. C-H activation for the construction of C-B bonds. Chem. Rev. 110, 890-931 (2010)
13. Gooen, L. J., Rodriguez, N. & Gooen, K. Carboxylic acids as substrates in homogeneous catalysis. Angew. Chem. Int. Ed. 47, 3100-3120 (2008)
14. Dzik, W., Lange, P. & Gooen, L. Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways. Chem. Sci. 3, 2671-2678 (2012)
15. Gooen, L. J., Deng, G. & Levy, L. M. Synthesis of biaryls via catalytic decarboxylative coupling. Science 313, 662-664 (2006)
16. Gooen, L. J. & Paetzoid, J. New synthesis of biaryls via Rh-catalyzed decarbonylative Suzuki-coupling of carboxylic anhydrides with arylboroxines. Adv. Synth. Catal. 346, 1665-1668 (2004)
17. Wang, J., Liu, B., Zhao, H. & Wang, J. Rhodium-catalyzed cross-coupling reactions of carboxylate and organoboron compounds via chelation-assisted C-C bond activation. Organometallics 31, 8598-8607 (2012)
18. Trost, B. & Chen, F. Transition metal mediated eliminations in anhydrides and thioanhydrides. Tetrahedron Lett. 28, 2603-2607 (1971)
19. O'Brien, E. M., Bercot, E. A. & Rovis, T. Decarbonylative cross-coupling of cyclic anhydride: introducing stereochemistry at an sp3 carbon in the cross-coupling event. J. Am. Chem. Soc. 125, 10498-10499 (2003)
20. Havlik, S., Simmons, J., Winton, V. & Johnson, J. Nickel-mediated decarbonylative cross-coupling of phthalimides with in situ generated diorganozinc reagents. J. Org. Chem. 76, 3588-3593 (2011)
21. Yamamoto, T., Ishizu, J., Kohara, T., Komiya, S. & Yamamoto, A. Oxidative addition of aryl carboxylates to nickel(0) complexes involving cleavage of the acyl-oxygen bond. J. Am. Chem. Soc. 102, 3758-3764 (1980)
22. Amaike, K., Muto, K., Yamaguchi, J. & Itami, K. Decarbonylative C-H coupling of azoles and aryl esters: unprecedented nickel catalysis and application to the synthesis of muscoride A. J. Am. Chem. Soc. 134, 13573-13576 (2012)
23. Hong, X., Liang, Y. & Houk, K. N. Mechanisms and origins of switchable chemoselectivity of Ni-catalyzed C(aryl)-O and C(acyl)-O activation of aryl esters with phosphine ligands. J. Am. Chem. Soc. 136, 2017-2025 (2014)
24. Lu, Q., Yu, H. & Fu, Y. Mechanistic study of chemoselectivity in Ni-catalyzed coupling reactions between azoles and aryl carboxylates. J. Am. Chem. Soc. 136, 8252-8260 (2014)
25. Xu, H. et al. Key mechanistic features of Ni-catalyzed C-H/C-O biaryl coupling of azoles and naphthalene-2-yl pivalates. J. Am. Chem. Soc. 136, 14834-14844 (2014)
26. Tasker, S. Z., Standley, E. A. & Jamison, T. F. Recent advances in homogeneous nickel catalysis. Nature 509, 299-309 (2014)
27. Yamaguchi, J., Muto, K. & Itami, K. Recent progress in nickel-catalyzed biaryl coupling. Eur. J. Org. Chem. 19-30 (2013)
28. Nakao, Y., Oda, S. & Hiyama, T. Nickel-catalyzed arylcyanation of alkynes. J. Am. Chem. Soc. 126, 13904-13905 (2004)
29. Watson, M. P. & Jacobsen, E. N. Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation. J. Am. Chem. Soc. 130, 12594-12595 (2008)
30. Murakami, M., Ashida, S. & Matsuda, T. Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones. J. Am. Chem. Soc. 127, 6932-6933 (2005)
31. Muto, K., Yamaguchi, J. & Itami, K. Nickel-catalyzed C-H/C-O coupling of azoles with phenol derivatives. J. Am. Chem. Soc. 134, 169-172 (2012)
32. Meng, L., Kamada, Y., Muto, K., Yamaguchi, J. & Itami, K. C-H alkenylation of azoles with enols and esters by nickel catalysis. Angew. Chem. Int. Ed. 52, 10048-10051 (2013)
33. Muto, K., Yamaguchi, J., Lei, A. & Itami, K. Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling. J. Am. Chem. Soc. 135, 16384-16387 (2013)
34. Takise, R., Muto, K., Yamaguchi, J. & Itami, K. Nickel-catalyzed a-arylation of ketones with phenol derivatives. Angew. Chem. Int. Ed. 53, 6791-6794 (2014)
35. Liu, L. et al. Mechanistic insight into the nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids: potassium phosphate is not a spectator base but is involved in the transmetalation step in the Suzuki-Miyaura reaction. Chem. Asian J. 8, 2592-2595 (2013)
36. Ananikov, V. P. Nickel: the ''spirited horse'' of transition metal catalysis. ACS Catal. 5, 1964-1971 (2015)
37. Figg, T. M., Wasa, M., Yu, J.-Q. & Musaev, D. G. Understanding the reactivity of Pd0/PR3-catalyzed intermolecular C(sp3)-H bond arylation. J. Am. Chem. Soc. 135, 14206-14214 (2013)
38. Petersen, T. B., Khan, R. & Olofsson, B. Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts. Org. Lett. 13, 3462-3465 (2011)
39. Battershill, A. J. & Scott, L. J. Telmisartan: a review of its use in the management of hypertension. Drugs 66, 51-83 (2006)
40. Quasdorf, K. W., Tian, X. & Garg, N. K. Cross-coupling reactions of aryl pivalates with boronic acids. J. Am. Chem. Soc. 130, 14422-14423 (2008)
41. Guan, B.-T., Wang, Y., Li, B.-J., Yu, D.-G. & Shi, Z.-J. Biaryl construction via Ni-catalyzed C-O activation of phenolic carboxylates. J. Am. Chem. Soc. 130, 14468-14470 (2008)
42. Tobisu, M., Shimasaki, T. & Chatani, N. Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters. Angew. Chem. Int. Ed. 47, 4866-4869 (2008)
43. Antoft-Finch, A., Blackburn, T. & Snieckus, V. N, N-Diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner. J. Am. Chem. Soc. 131, 17750-17752 (2009)