Titanium-Catalyzed Multicomponent Couplings: Efficient One-Pot Syntheses of Nitrogen Heterocycles

Accounts of Chemical Research

Volumn 48, Issue 11, 2015, Pages 2822-2833

  Odom, Aaron L ^a   McDaniel, Tanner J ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84947271700     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00280     Document Type: Article

References (40)

1. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements, 1 st ed.; Pergamon Press: Oxford, 1984.
2. Nakamura, I.; Yamamoto, Y. Transition-metal-catalyzed reactions in heterocyclic synthesis Chem. Rev. 2004, 104, 2127-2198 10.1021/cr020095i
3. Mathew, S.; Yella, A.; Gao, Y.; Humphry-Baker, R.; Curchod, B. F. E.; Ashari-Astani, N.; Tavernelli, I.; Rothlisberger, U.; Nazeeruddin, M. K.; Grätzel, M. Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers Nat. Chem. 2014, 6, 242-247 10.1038/nchem.1861
4. Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Synthesis, Structure, and Reactivity of Aryloxo(imido)titanium Complexes Angew. Chem., Int. Ed. Engl. 1990, 29, 664-665 10.1002/anie.199006641
5. 2Zr = NR) Complexes J. Am. Chem. Soc. 1988, 110, 8729-8731 10.1021/ja00234a043
6. 2 J. Am. Chem. Soc. 1992, 114, 1708-1719 10.1021/ja00031a026
7. 2]-catalyzed intermolecular hydroamination of alkynes Angew. Chem., Int. Ed. 2001, 40, 2305-2308 10.1002/1521-3773(20010618)40:12<2305::AID-ANIE2305>3.0.CO;2-7
8. 4 as a Precatalyst for Hydroamination of Alkynes with Primary Amines Organometallics 2001, 20, 3967-3969 10.1021/om010566b
9. Tommos, C.; Babcock, G. T. Proton and hydrogen currents in photosynthetic water oxidation Biochim. Biophys. Acta, Bioenerg. 2000, 1458, 199-219 10.1016/S0005-2728(00)00069-4
10. Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G. Proton-coupled electron transfer: a unifying mechanism for biological charge transport, amino acid radical initiation and propagation, and bond making/breaking reactions of water and oxygen Biochim. Biophys. Acta, Bioenerg. 2004, 1655, 13-28 10.1016/j.bbabio.2003.08.010
11. Bemowski, R. D.; Singh, A. K.; Bajorek, B. J.; DePorre, Y.; Odom, A. L. Effective donor abilities of E-t-Bu and EPh (E = O, S, Se, Te) to a high valent transition metal Dalton Trans 2014, 43, 12299-12305 10.1039/C4DT01314J
12. DiFranco, S. A.; Maciulis, N. A.; Staples, R. J.; Batrice, R. J.; Odom, A. L. Inorg. Chem. 2012, 51, 1187-1200 10.1021/ic202524r
13. 2(dpma) Inorg. Chem. 2004, 43, 3605-3617 10.1021/ic049644o
14. Li, Y.; Turnas, A.; Ciszewski, J. T.; Odom, A. L. Group-4 η1-pyrrolyl complexes incorporating N,N-di(pyrrolyl-α-methyl)-N-methylamine Inorg. Chem. 2002, 41, 6298-6306 10.1021/ic0259484
15. Shi, Y.; Cao, C.; Odom, A. L. Synthesis and group-4 complexes of tris(pyrrolyl-α-methyl)amine Inorg. Chem. 2004, 43, 275-281 10.1021/ic035049v
16. Freedman, D. E.; Harman, W. H.; Harris, T. D.; Long, G. J.; Chang, C. J.; Long, J. R. Slow magnetic relaxation in a high-spin iron(II) complex J. Am. Chem. Soc. 2010, 132, 1224-1225 10.1021/ja909560d
17. Cao, C.; Shi, Y.; Odom, A. L. Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines Org. Lett. 2002, 4, 2853-2856 10.1021/ol0201052
18. Shi, Y.; Hall, C.; Ciszewski, J. T.; Cao, C.; Odom, A. L. Titanium dipyrroylmethane derivatives: Rapid intermolecular alkyne hydroamination Chem. Commun. 2003, 586-587 10.1039/b212423h
19. Banerjee, S.; Barnea, E.; Odom, A. L. Titanium-catalyzed hydrohydrazination with monosubstituted hydrazines: Catalyst design, synthesis, and reactivity Organometallics 2008, 27, 1005-1014 10.1021/om700852v
20. Dissanayake, A. A.; Odom, A. L. Single-step synthesis of pyrazoles using titanium catalysis Chem. Commun. 2012, 48, 440-442 10.1039/C1CC15809K
21. Cao, C.; Ciszewski, J. T.; Odom, A. L. Hydroamination of alkynes catalyzed by a titanium pyrrolyl complex Organometallics 2001, 20, 5011-5013 10.1021/om010595m
22. Yim, J. C.-H.; Schafer, L. L. Efficient anti-Markovnikov-selective catalysts for intermolecular alkyne hydroamination: Recent advances and synthetic applications Eur. J. Org. Chem. 2014, 2014, 6825-6840 10.1002/ejoc.201402300
23. Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Hydroamination: Direct addition of amines to alkenes and alkynes Chem. Rev. 2008, 108, 3795-3892 10.1021/cr0306788
24. Severin, R.; Doye, S. The catalytic hydroamination of alkynes Chem. Soc. Rev. 2007, 36, 1407-1420 10.1039/b600981f
25. Odom, A. L. New C-N and C-C bond forming reactions catalyzed by titanium complexes Dalton Trans. 2005, 225-233 10.1039/b415701j
26. Cao, C.; Li, Y.; Shi, Y.; Odom, A. L. α,β-Unsaturated imines form titanium hydroamination and functionalization by rhodium C-H activation Chem. Commun. 2004, 2002-3 10.1039/b405620e
27. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Rhodium catalyzed chelation-assisted C-H bond functionalization reactions Acc. Chem. Res. 2012, 45, 814-825 10.1021/ar200190g
28. Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Pyrrole syntheses based on titanium-catalyzed hydroamination of diynes Org. Lett. 2004, 6, 2957-2960 10.1021/ol0489088
29. Thinking the term to be a mouthful at the time, we did not use "hydrohydrazination" in ref 16. It was perhaps first used in the literature here: Waser, J.; Carreira, E. M. Convenient synthesis of alkylhydrazies by the cobalt-catalyzed hydrohydrazination reaction of olefins and azodicarboxylates J. Am. Chem. Soc. 2004, 126, 5676-5677 10.1021/ja048698u
30. Patel, S.; Li, Y.; Odom, A. L. Synthesis, structure, and LLCT transitions in terminal hydrazido(2-) bipyridine complexes of titanium Inorg. Chem. 2007, 46, 6373-6381 10.1021/ic700426s
31. Banerjee, S.; Odom, A. L. Synthesis and structure of a titanium hydrazido(2-) complex Organometallics 2006, 25, 3099-3101 10.1021/om060304f
32. β bond cleavage Chem.-Eur. J. 2011, 17, 265-285 10.1002/chem.201002776
33. Vujokovic, N.; Fillol, J. L.; Ward, B. D.; Wadepohl, H.; Mountford, P.; Gade, L. H. Insertions into azatitanacyclobutenes: New insights into three component coupling reactions involving imidotitanium intermediates Organometallics 2008, 27, 2518-2528 10.1021/om8001203
34. Cao, C.; Shi, Y.; Odom, A. L. A titanium-catalyzed three-component coupling to generate α,β-unsaturated β-iminoamines J. Am. Chem. Soc. 2003, 125, 2880-2881 10.1021/ja0284714
35. Barnea, E.; Majumder, S.; Staples, R. J.; Odom, A. L. One-step route to 2,3-diaminopyrroles using a titanium-catalyzed four-component coupling Organometallics 2009, 28, 3876-3881 10.1021/om9001928
36. Majumder, S.; Gipson, K. R.; Staples, R. J.; Odom, A. L. Pyrazole synthesis using a titanium-catalyzed multicomponent coupling reaction and synthesis of withasomnine Adv. Synth. Catal. 2009, 351, 2013-2023 10.1002/adsc.200900293
37. Majumder, S.; Odom, A. L. Titanium catalyzed one-pot multicomponent coupling reactions for direct access to substituted pyrimidines Tetrahedron 2010, 66, 3152-3158 10.1016/j.tet.2010.02.066
38. Dissanayake, A. A.; Odom, A. L. Regioselective conversion of alkynes to 4-substituted and 3,4-disubstituted isoxazoles using titanium-catalyzed multicomponent coupling reactions Tetrahedron 2012, 68, 807-812 10.1016/j.tet.2011.11.043
39. Majumder, S.; Gipson, K. R.; Odom, A. L. A multicomponent coupling sequence for direct access to substituted quinolines Org. Lett. 2009, 11, 4720-4723 10.1021/ol901855b
40. Dissanayake, A. A.; Staples, R. J.; Odom, A. L. Titanium-catalyzed, one-pot synthesis of 2-amino-3-cyanopyridines Adv. Synth. Catal. 2014, 356, 1811-1822 10.1002/adsc.201301046