Kumada-Grignard-type biaryl couplings on water

Nature Communications

Volumn 6, Issue , 2015, Pages

  Bhattacharjya, Anish ^a   Klumphu, Piyatida ^a   Lipshutz, Bruce H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GRIGNARD REAGENT; HALIDE; MAGNESIUM; PALLADIUM; WATER; BROMINATED HYDROCARBON; HYDROCARBON; IODINATED HYDROCARBON;

CATALYSIS; HALIDE; LEAD; MAGNESIUM; SOLVENT;

AROMATIZATION; ARTICLE; CATALYST; CONTROLLED STUDY; CROSS COUPLING REACTION; ELECTRON; ELECTROPHILICITY; HEATING; KUMADA CROSS COUPLING; MASS FRAGMENTOGRAPHY; ROENTGEN SPECTROSCOPY; CATALYSIS; CHEMISTRY;

CATALYSIS; HYDROCARBONS, BROMINATED; HYDROCARBONS, CYCLIC; HYDROCARBONS, IODINATED; MAGNESIUM; PALLADIUM; WATER;

EID: 84935018475     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms8401     Document Type: Article

References (25)

1. Vollhardt, K. P. C. & Schore, N. E. Organic Chemistry: Structure and Function 6 edn 305 (W.H. Freeman, 2011).
2. Krasovskiy, A., Duplais, C. & Lipshutz, B. H. Zn-mediated, Pd-catalyzed crosscouplings in water at room temperature without prior formation of organozinc reagents. J. Am. Chem. Soc. 131, 15592-15593 (2009).
3. Krasovskiy, A., Duplais, C. & Lipshutz, B. H. Stereoselective Negishi-like couplings between alkenyl and alkyl halides in water at room temperature. Org. Lett. 12, 4742-4744 (2010).
4. Duplais, C., Krasovskiy, A., Wattenberg, A. & Lipshutz, B. H. Cross-couplings between benzylic and aryl halides on water: synthesis of diarylmethanes. Chem. Commun. 46, 562-564 (2010).
5. Duplais, C., Krasovskiy, A. & Lipshutz, B. H. Organozinc chemistry enabled by micellar catalysis. Palladium-catalyzed cross-couplings between alkyl and aryl bromides in water at room temperature. Organometallics 30, 6090-6097 (2011).
6. Krasovskaya V. Krasovskiy A. Bhattacharjya A. Lipshutz B.H. On water sp3-sp2 cross-couplings between benzylic and alkenyl halides Chem. Commun 2011 47 5717-5719
7. Zhou, F. & Li, C.-J. The Barbier-Grignard-type arylation of aldehydes using unactivated aryl iodides in water. Nat. Commun. 5, 4254 (2014).
8. Gosmini, C., Bassene-Ernst, C. & Durandetti, M. Synthesis of functionalized 2-arylpyridines from 2-halopyridines and various aryl halides via a nickel catalysis. Tetrahedron 65, 6141-6146 (2009).
9. Qian, Q. et al. Nickel-catalyzed reductive cross-coupling of aryl halides. Synlett 24, 619-624 (2013).
10. Giovannini, R., Stüdemann, T., Dussin, G. & Knochel, P. An efficient nickelcatalyzed cross-coupling between sp3 carbon centers. Angew. Chem. Int. Ed. 37, 2387-2390 (1998).
11. Lipshutz, B. H. et al. TPGS-750-M: a second-generation amphiphile for metalcatalyzed cross-couplings in water at room temperature. J. Org. Chem. 76, 4379-4391 (2011).
12. Klumphu, P. & Lipshutz, B. H. "Nok": a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature. J. Org. Chem. 79, 888-900 (2014).
13. Creutz, S. E., Lotito, K. J., Fu, G. C. & Peters, J. C. Photoinduced Ullmann C-N coupling: demonstrating the viability of a radical pathway. Science 338, 647-651 (2012).
14. Wang, P., Shi, X., Kataoka, K., Maeda, Y. & Kobiro, K. Non-catalytic Oppenauer oxidation of alcohols in supercritical water. J. Supercrit. Fluids 52, 222-227 (2010).
15. Evans, J. et al. Structural characterisation of solution species implicated in the palladium-catalysed Heck reaction by Pd K-edge X-ray absorption spectroscopy: palladium acetate as a catalyst precursor. J. Chem. Soc, Dalton Trans. 10, 2207-2212 (2002).
16. de Vries, J. G. A unifying mechanism for all high-temperature Heck reactions. The role of palladium colloids and anionic species. Dalton Trans. 421-429 (2006).
17. de Vries, A. H. M. et al. A practical recycle of a ligand-free palladium catalyst for heck reactions. Adv. Synth. Catal. 344, 996-1002 (2002).
18. Reetz, M. T. & Westermann, E. Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles. Angew. Chem. Int. Ed. 39, 165-168 (2000).
19. Knappke, C. E. I. et al. Reductive cross-coupling reactions between two electrophiles. Chem. Eur. J. 20, 6828-6842 (2014).
20. Tucker, J. L. Green chemistry, a pharmaceutical perspective. Org. Process Res. Dev. 10, 315-319 (2006).
21. Dunn, P., Henderson, R., Mergelsberg, I. & Wells, A. Collaboration to Deliver a Solvent Selection Guide for the Pharmaceutical Industry Moving towards Greener Solvents for Pharmaceutical Manufacturing-An Industry Perspective (ACS Green Chemistry Institute Pharmaceutical, 2009http://acs.confex.com/ acs/green09/recordingredirect.cgi/id/510.
22. Eissen, M., Hungerbuhler, K., Dirks, S. & Metzger, J. Mass efficiency as metric for the effectiveness of catalysts. Green Chemistry 5, G25-G27 (2003).
23. Jiménez-González, C., Curzons, A., Constable, D. C. & Cunningham, V. Cradle-to-gate life cycle inventory and assessment of pharmaceutical compounds. Int. J. Life Cycle Assess. 9, 114-121 (2004).
24. Nising, C. F., Schmid, U. K., Nieger, M. & Bräse, S. A new protocol for the one-pot synthesis of symmetrical biaryls. J. Org. Chem. 69, 6830-6833 (2004).
25. Bernhardt, S., Manolikakes, G., Kunz, T. & Knochel, P. Preparation of solid salt-stabilized functionalized organozinc compounds and their application to cross-coupling and carbonyl addition reactions. Angew. Chem. Int. Ed. 50, 9205-9209 (2011).