Cobalt-catalysed site-selective intra-and intermolecular dehydrogenative amination of unactivated sp3carbons

Nature Communications

Volumn 6, Issue , 2015, Pages

  Wu, Xuesong ^a   Yang, Ke ^b   Zhao, Yan ^a   Sun, Hao ^b   Li, Guigen ^b,c   Ge, Haibo ^a  

^a INDIANA UNIVERSITY   (United States)

^b NANJING UNIVERSITY   (China)

^c TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBON; CHLOROBENZENE; COBALT; COBALT COMPLEX; FUNCTIONAL GROUP; PROPIONAMIDE DERIVATIVE;

AMMONIUM COMPOUND; CARBON; CATALYSIS; COBALT; HYDROGEN;

AMIDATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HUMAN; METALLATION; OXIDATION; PROTON TRANSPORT; SIDE EFFECT; STEREOCHEMISTRY;

EID: 84924371284     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms7462     Document Type: Article

References (69)

1. Daugulis, O., Do, H.-Q. & Shabashov, D. Palladium-and copper-catalyzed arylation of carbon-hydrogen bonds. Acc. Chem. Res. 42, 1074-1086 (2009).
2. 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).
3. Colby, D. A., Bergman, R. G. & Ellman, J. A. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem. Rev. 110, 624-655 (2010).
4. Lyons, T. W. & Sanford, M. S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev. 110, 1147-1169 (2010).
5. Jazzar, R., Hitce, J., Renaudat, A., Sofack-Kreutzer, J. & Baudoin, O. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation. Chem. Eur. J. 16, 2654-2672 (2010).
6. Yeung, C. S. & Dong, V. M. Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds. Chem. Rev. 111, 1215-1292 (2011).
7. Ackermann, L. Carboxylate-assisted transition-metal-catalyzed C-H bond functionalizations: mechanism and scope. Chem. Rev. 111, 1315-1345 (2011).
8. Davis, H. M. L., Du Bois, J. & Yu, J.-Q. C-H functionalization in organic synthesis. Chem. Soc. Rev. 40, 1855-1856 (2011).
9. Gutekunst, W. R. & Baran, P. S. C-H functionalization logic in total synthesis. Chem. Soc. Rev. 40, 1976-1991 (2011).
10. Hartwig, J. F. Regioselectivity of the borylation of alkanes and arenes. Chem. Soc. Rev. 40, 1992-2002 (2011).
11. White, M. C. Adding aliphatic C-H bond oxidations to synthesis. Science 335, 807-809 (2012).
12. Yamaguchi, J., Yamaguchi, A. D. & Itami, K. C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals. Angew. Chem. Int. Ed. 51, 8960-9009 (2012).
13. Collins, K. & Glorius, F. A robustness screen for the rapid assessment of chemical reactions. Nat. Chem 5, 597-601 (2013).
14. Hess, W., Treutwein, J. & Hilt, G. Cobalt-catalysed carbon-carbon bondformation reactions. Synthesis 3537-3562 (2008).
15. Kulkarni, A. A. & Daugulis, O. Direct conversion of carbon-hydrogen into carbon-carbon bonds by first-row transition-metal catalysis. Synthesis 4087-4109 (2009).
16. Yoshikai, N. Chiral-auxiliary-controlled diastereoselective epoxidations. Synlett 1047-1051 (2011).
17. Gao, K. & Yoshikai, N. Low-valent cobalt catalysis: new opportunities for C-H functionalization. Acc. Chem. Res. 47, 1208-1219 (2014).
18. Murahashi, S. Synthesis of phthalimidines from schiff bases and carbon monoxide. J. Am. Chem. Soc. 77, 6403-6404 (1955).
19. Murahashi, S. & Horiie, S. The reaction of azobenzene and carbon monoxide. J. Am. Chem. Soc. 78, 4816-4817 (1956).
20. Funk, J., Yennawar, H. & Sen, A. Cobalt-catalyzed carbonylation of N-alkylbenzaldimines to 'N-alkylphthalimidines' (2,3-dihydro-1H-isoindol-1-ones) via tandem C-H activation and cyclocarbonylation. Helv. Chim. Acta 89, 1687-1695 (2006).
21. Lee, P.-S., Fujita, T. & YoshikaI, N. Cobalt-catalyzed, room-temperature addition of aromatic imines to alkynes via directed C-H bond activation. J. Am. Chem. Soc. 133, 17283-17295 (2011).
22. Gao, K., Lee, P.-S., Fujita, T. & Yoshikai, N. Cobalt-catalyzed hydroarylation of alkynes through chelation-assisted C-H bond activation. J. Am. Chem. Soc. 132, 12249-12251 (2010).
23. Ding, Z.-H. & Yoshikai, N. Cobalt-catalyzed addition of azoles to alkynes. Org. Lett. 12, 4180-1283 (2010).
24. Chen, Q., Ilies, L. & Nakamura, E.-I. Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C-H bond activation. J. Am. Chem. Soc. 133, 428-429 (2011).
25. Li, B. et al. Direct cross-coupling of C-H bonds with Grignard reagents through cobalt catalysis. Angew. Chem. Int. Ed. 50, 1109-1113 (2011).
26. Gao, K. & YoshikaI, N. Cobalt-catalyzed ortho-alkylation of aromatic imines with primary and secondary alkyl halides. J. Am. Chem. Soc. 135, 9279-9282 (2013).
27. Yao, T., Hirano, K., Satoh, T. & Miura, M. Nickel-and cobalt-catalyzed direct alkylation of azoles with N-tosylhydrazones bearing unactivated alkyl groups. Angew. Chem. Int. Ed. 51, 775-779 (2012).
28. Yoshino, T., Ikemoto, H., Matsunaga, S. & Kanai, M. A cationic high-valent Cp CoIII complex for the catalytic generation of nucleophilic organometallic species: directed C-H bond activation. Angew. Chem. Int. Ed. 52, 2207-2211 (2013).
29. Ikemoto, H., Yoshino, T., Sakata, K., Matsunaga, S. & Kanai, M. Pyrroloindolone synthesis via a Cp CoIII-catalyzed redox-neutral directed C-H alkenylation/annulation sequence. J. Am. Chem. Soc. 136, 5424-5431 (2014).
30. Grigorjeva, L. & Daudulis, O. Cobalt-catalyzed, aminoquinoline-directed C(sp2)-H bond alkenylation by alkynes. Angew. Chem. Int. Ed. 53, 10209-10212 (2014).
31. Lenges, C. P., White, P. S. & Brookhart, M. Mechanistic and synthetic studies of the addition of alkyl aldehydes to vinylsilanes catalyzed by Co(I) complexes. J. Am. Chem. Soc. 120, 6965-6979 (1998).
32. Cenini, S., Tollari, S., Penoni, A. & Cereda, C. Catalytic amination of unsaturated hydrocarbons: reactions of p-nitrophenyl azide with alkenes catalyzed by metalloporphyrins. J. Mol. Catal 137, 135-146 (1999).
33. Ragaini, F. et al. Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes: a synthetic and mechanistic study. Chem. Eur. J. 9, 249-259 (2003).
34. Lu, H.-J. & Zhang, X. P. Catalytic C-H functionalization by metalloporphyrins: recent developments and future directions. Chem. Soc. Rev. 40, 1899-1909 (2011).
35. Lu, H.-J., Li, C.-Q., Jiang, H.-L., Lizardi, C. L. & Zhang, X. P. Chemoselective amination of propargylic C(sp3)-H bonds by cobalt(II)-based metalloradical catalysis. Angew. Chem. Int. Ed. 53, 7028-7032 (2014).
36. Dick, A. R. & Sanford, M. S. Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds. Tetrahedron 62, 2439-2463 (2006).
37. Boutadla, Y., Davies, D. L., Macgregor, S. A. & Poblador-Bahamonde, A. I. Mechanisms of C-H bond activation: rich synergy between computation and experiment. Dalton Trans. 5820-5831 (2009).
38. Bolig, A. D. & Brookhart, M. Activation of sp3 C-H bonds with cobalt(I): catalytic synthesis of enamines. J. Am. Chem. Soc. 129, 14544-14545 (2007).
39. Hung-Low, F., Krogman, J. P., Tye, J. W. & Bradley, C. A. Development of more labile low electron count Co(I) sources: mild, catalytic functionalization of activated alkanes using a [(Cp Co)2-m-(Z4:Z4-arene)] complex. Chem. Commun. 48, 368-370 (2012).
40. Lyons, T. W. & Brookhart, M. Cobalt-catalyzed hydrosilation/hydrogentransfer cascade reaction: a new route to silyl enol ethers. Chem. Eur. J. 19, 10124-10127 (2013).
41. Corbet, M. & De Campo, F. 8-Aminoquinoline: a powerful directing group in metal-catalyzed direct functionalization of C-H bonds. Angew. Chem. Int. Ed. 52, 9896-9898 (2013).
42. Rouquet, G. & Chatani, N. Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds by using bidentate directing groups. Angew. Chem. Int. Ed. 52, 11726-11743 (2013).
43. Tahlan, K. & Jensen, S. E. J. Origins of the b-lactam rings in natural products. Antibiotic 66, 401-410 (2013).
44. Ye, L.-W., Shu, C. & Gagosz, F. Recent progress towards transition metalcatalyzed synthesis of g-lactams. Org. Biomol. Chem. 12, 1833-1845 (2014).
45. He, G., Zhang, S.-Y., Nack, W. A., Li, Q. & Chen, G. Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated g C(sp3)-H bonds. Angew. Chem. Int. Ed. 52, 11124-11128 (2013).
46. Zhang, Q. et al. Stereoselective synthesis of chiral a-amino-b-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp3)-H bonds. Angew. Chem. Int. Ed. 52, 13588-13592 (2013).
47. McNally, A., Haffemayer, B., Collins, B. S. & Gaunt, M. J. Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles. Nature 510, 129-133 (2014).
48. Sun, W.-W. et al. Palladium-catalyzed unactivated C(sp3)-H bond activation and intramolecular amination of carboxamides: a new approach to b-lactams. Org. Lett. 16, 480-483 (2014).
49. Wang, Z., Ni, J.-Z., Kuninobu, Y. & Kanai, M. Copper-catalyzed intramolecular C(sp3)-H and C(sp2)-H amidation by oxidative cyclization. Angew. Chem. Int. Ed. 53, 3496-3499 (2014).
50. Wu, X.-S., Zhao, Y., Zhang, G.-W. & Ge, H.-B. Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds. Angew. Chem. Int. Ed. 53, 3706-3710 (2014).
51. Wu, X.-S., Zhao, Y. & Ge, H.-B. Nickel-catalyzed site-selective amidation of unactivated C(sp3)-H bonds. Chem. Eur. J. 20, 9530-9533 (2014).
52. Yang, M. et al. Silver-catalysed direct amination of unactivated C-H bonds of functionalized molecules. Nat. Commun 5, 4707-4712 (2014).
53. Lewis, R. A. et al. Synthesis of a cobalt(IV) ketimide with a squashed tetrahedral geometry. Chem. Commun. 49, 2888-2890 (2013).
54. Nguyen, A. I., Hadt, R. G., Solomon, E. I. & Tilley, T. D. Efficient C-H bond activations via O2 cleavage by a dianionic cobalt(II) complex. Chem. Sci. 5, 2874-2878 (2014).
55. Théveau, L. et al. Mechanism selection for regiocontrol in base-assisted, palladium-catalysed direct C-H coupling with halides: first approach for oxazole-and thiazole-4-carboxylates. Chem. Eur. J. 17, 14450-14463 (2011).
56. Aihara, Y. & Chatani, N. Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance. J. Am. Chem. Soc. 136, 898-901 (2014).
57. Brunschwig, B. S., Chou, M.-H., Creutz, C., Ghosh, P. & Sutin, N. Mechanisms of water oxidation to oxygen: cobalt(IV) as an intermediate in the aquocobalt(II)-catalyzed reaction. J. Am. Chem. Soc. 105, 4832-4833 (1983).
58. Anson, F. C., Collins, T. J., Coots, R. J., Gipson, S. L. & Richmond, T. G. Synthesis and characterization of stable cobalt(IV) coordination complexes: molecular structure of trans-[Z4-1,2-bis(3,5-dichloro-2-hydroxybenzamido)-4,5-dichlorobenzene]bis(4-tert-butylpyridine)cobalt(IV). J. Am. Chem. Soc. 106, 5037-5038 (1984).
59. Collet, F., Dodd, R. H. & Dauban, P. Catalytic C-H amination: recent progress and future directions. Chem. Commun. 5061-5074 (2009).
60. Ramirez, T. A., Zhao, B. & Shi, Y. Recent advances in transition metal-catalyzed sp3 C-H amination adjacent to double bonds and carbonyl groups. Chem. Soc. Rev. 41, 931-942 (2012).
61. Jeffrey, J. L. & Sarpong, R. Intramolecular C(sp3)-H amination. Chem. Sci 4, 4092-4106 (2013).
62. Thu, H. Y., Yu, W. Y. & Che, C. M. Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion. J. Am. Chem. Soc. 128, 9048-9049 (2006).
63. Pan, J., Su, M. & Buchwald, S. L. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp3)-H bonds. Angew. Chem. Int. Ed. 50, 8647-8651 (2011).
64. Iglesias, Á ., Álvarez, R., de Lera, Á . R. & Muñiz, K. Palladium-catalyzed intermolecular C(sp3)-H amidation. Angew. Chem. Int. Ed. 51, 2225-2228 (2012).
65. Kang, T., Kim, Y., Lee, D., Wang, Z. & Chang, S. Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: late-stage functionalization of an unactivated methyl group. J. Am. Chem. Soc. 136, 4141-4144 (2014).
66. Wang, N. et al. Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp3)-H functionalization. J. Org. Chem. 79, 5379-5385 (2014).
67. Kang, T., Kim, H., Kim, J. G. & Chang, S. Facile one step-synthesis and characterisation of high aspect ratio core-shell copper-polyaniline nanowires. Chem. Commun. 50, 1207-1212 (2014).
68. Sun, H., Zhang, H.-W., Han, J.-L., Pan, Y. & Li, G. Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of a,b-syn-diamino acid derivatives. Eur. J. Org. Chem. 22, 4744-4747 (2013).
69. Pindi, S., Wu, J.-B. & Li, G. Design, synthesis and applications of new chiral N-2-phenyl-2-propyl sulfinylimines for Group-Assisted Purification (GAP) asymmetric synthesis. J. Org. Chem. 78, 4006-4012 (2013).