Sequential coupling approach to the synthesis of nickel(II) complexes with N-aryl-2-amino phenolates

ACS Combinatorial Science

Volumn 14, Issue 10, 2012, Pages 545-550

  Fuse, Shinichiro ^a   Tago, Hiroaki ^a   Maitani, Masato M ^a   Wada, Yuji ^a   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Combinatorial libraries; N aryl 2 amino phenol; Near IR absorption; Nickel(II) complex; Sequential multicomponent coupling; Suzuki Miyaura coupling

Indexed keywords

AMINOPHENOL DERIVATIVE; NICKEL; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

AMINOPHENOLS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS;

EID: 84870272212     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co3000665     Document Type: Article

References (26)

1. Miyaura, N.; Suzuki, A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J. Chem. Soc., Chem. Commun. 1979, 866.
2. Miyaura, N.; Yamada, K.; Suzuki, A. New stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkyunyl halides. Tetrahedron Lett. 1979, 3437.
3. Gray, G. W.; Hird, M.; Lacey, D.; Toyne, K. J. The synthesis and transition-temperatures of some 4,4″-dialkyl-1,1′-4′,1″- terphenyl and 4,4″-alkoxyalkyl-1,1′-4′,1″-terphenyl with 2,3-difluoro or 2′,3′-difluoro substituents and of their biphenyl analogs. J. Chem. Soc., Perkin Trans. 2 1989, 2041.
4. Unrau, C. M.; Campbell, M. G.; Snieckus, V. Directed ortho-metalation- Suzuki cross coupling connections - convenient regiospecific routes to functionalized meta-tetraryls and para-teraryls and meta-quinquearyls. Tetrahedron Lett. 1992, 33, 2773.
5. Hird, M.; Lewis, R. A.; Toyne, K. J.; West, J. J.; Wilson, M. K. The synthesis of novel highly substituted benzene derivatives for use in palladium-catalysed cross-coupling reactions. J. Chem. Soc., Perkin Trans. 1 1998, 3479.
6. Bo, Z. S.; Schluter, A. D. Synthesis of low-generation, aryl-/alkyl-type, nonpolar dendrons carrying protected hydroxyalkyl groups in the periphery. J. Org. Chem. 2002, 67, 5327.
7. Voisin-Chiret, A. S.; Muraglia, M.; Burzicki, G.; Perato, S.; Corbo, F.; Santos, J. S. D.; Franchini, C.; Rault, S. Synthesis of new phenylpyridyl scaffolds using the Garlanding approach. Tetrahedron 2010, 66, 8000.
8. Rossi, R.; Bellina, F.; Lessi, M. Highly selective palladium-catalyzed Suzuki-Miyaura monocoupling reactions of ethene and arene derivatives bearing two or more electrophilic sites. Tetrahedron 2011, 67, 6969.
9. Chaudhuri, P.; Verani, C. N.; Bill, E.; Bothe, E.; Weyhermuller, T.; Wieghardt, K. Electronic structure of bis(O-iminobenzosemiquinonato)-metal complexes (Cu, Ni, Pd). The art of establishing physical oxidation states in transition-metal complexes containing radical ligands. J. Am. Chem. Soc. 2001, 123, 2213.
10. Bachler, V.; Olbrich, G.; Neese, F.; Wieghardt, K. Theoretical evidence for the singlet diradical character of square planar nickel complexes containing two omicron-semiquinonato type ligands. Inorg. Chem. 2002, 41, 4179.
11. Min, K. S.; Weyhermuller, T.; Bothe, E.; Wieghardt, K. Tetradentate bis(O-iminobenzosemiquinonate(1-)) π radical ligands and their O-aminophenolate(1-) derivatives in complexes of nickel(II), palladium(II), and copper(II). Inorg. Chem. 2004, 43, 2922.
12. Fukui, H.; Kishi, R.; Minami, T.; Nagai, H.; Takahashi, H.; Kubo, T.; Kamada, K.; Ohta, K.; Champagne, B.; Botek, E.; Nakano, M. Theoretical study on second hyperpolarizabilities of singlet diradical square planar nickel complexes involving O-semiquinonato type ligands. J. Phys. Chem. A 2008, 112, 8423.
13. Mukherjee, C.; Weyhermuller, T.; Bothe, E.; Chaudhuri, P. Targeted oxidase reactivity with a new redox-active ligand incorporating N(2)O(2) donor atoms. complexes of Cu(II), Ni(II), Pd(II), Fe(III), and V(V). Inorg. Chem. 2008, 47, 11620.
14. Sato, W.; Saito, Y. Patent WO 2005/02213 A1, 2005.
15. Takahashi, T.; Kusaka, S.; Doi, T.; Sunazuka, T.; Omura, S. A combinatorial synthesis of a macrosphelide library utilizing a palladium- catalyzed carbonylation on a polymer support. Angew. Chem., Int. Ed. 2003, 42, 5230.
16. Doi, T.; Inoue, H.; Tokita, M.; Watanabe, J.; Takahashi, T. Sequential palladium-catalyzed coupling reactions on solid-phase. J. Comb. Chem. 2008, 10, 135.
17. Yoshida, M.; Doi, T.; Kang, S. M.; Watanabe, J.; Takahashi, T. Solid-phase combinatorial synthesis of ester-type banana-shaped molecules by sequential palladium-catalyzed carbonylation. Chem. Commun. 2009, 2756.
18. Serizawa, T.; Miyamoto, S.; Numajiri, Y.; Fuse, S.; Doi, T.; Takahashi, T. Stereoselective one-pot three-component coupling approach towards the synthesis of the AC ring system of taxanes. Tetrahedron Lett. 2009, 50, 3408.
19. Fuse, S.; Sugiyama, S.; Takahashi, T. Rapid assembly of resorcylic acid lactone frameworks through sequential palladium-catalyzed coupling reactions. Chem. - Asian J. 2010, 5, 2459.
20. Sugiyama, S.; Fuse, S.; Takahashi, T. Three-component coupling approach toward the synthesis of a resorcylic acid lactone framework. Tetrahedron 2011, 67, 6654.
21. Fuse, S.; Masui, H.; Tannna, A.; Shimizu, F.; Takahashi, T. Combinatorial synthesis and evaluation of a-iminocarboxamide-nickel-(II) catalysts for the copolymerization of ethylene and apolar monomer. ACS Comb. Sci. 2012, 14, 17.
22. Shadyro, O. I.; Sorokin, V. L.; Ksendzova, G. A.; Polozov, G. I.; Nikolaeva, S. N.; Pavlova, N. I.; Savinova, O. V.; Boreko, E. I. Synthesis and antiviral activity of N-acyl derivatives of 4,6-di-(tert-butyl)-2-aminophenol. Pharm. Chem. J. 2003, 37, 399.
23. Kracker, H. Patent DE 580519, 1933.
24. Maslovskaya, L.A; Petrikevich, D. K.; Timoshchuk, V. A.; Shadyro, O. I. Synthesis and antioxidative properties of certain derivatives of alkylated pyrocatechin. Zh. Obshch. Khim. 1996, 66, 1893.
25. Kim, E.; Koh, M.; Lim, B. J.; Park, S. B. Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo 3,4-b indolizin-3-one. J. Am. Chem. Soc. 2011, 133, 6642.
26. Kim, E.; Koh, M.; Ryu, J.; Park, S. B. Combinatorial discovery of full-color-tunable emissive fluorescent probes using a single core skeleton, 1,2-dihydropyrrolo 3,4-beta indolizin-3-one. J. Am. Chem. Soc. 2008, 130, 12206.