Introduction of Hindered Electrophiles via C-H Functionalization in a Palladium-Catalyzed Multicomponent Domino Reaction

Synthesis (Germany)

Volumn 47, Issue 16, 2015, Pages 2446-2456

  Qureshi, Zafar ^a   Schlundt, Waldemar ^a   Lautens, Mark ^a  

^a Universitcny BRA of Toronto   (Canada)

Author keywords

C H functionalization; Catellani reaction; domino reaction; multicomponent reaction; palladium

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; PALLADIUM; REACTION KINETICS;

CATELLANI REACTION; DOMINO REACTIONS; FUNCTIONALIZATIONS; MULTI-COMPONENT DOMINO REACTION; MULTI-COMPONENT REACTIONS; ONE POT PROCESS; PALLADIUM-CATALYZED; STERICALLY CONGESTED;

SYNTHESIS (CHEMICAL);

ALKYL IODIDE DERIVATIVE; CARBON; ELECTROPHILE; HYDROGEN; IODINE DERIVATIVE; NORBORNENE DERIVATIVE; PALLADIUM; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; MEDIATOR; ONE POT SYNTHESIS; PROCESS OPTIMIZATION; STEREOCHEMISTRY;

EID: 84938745826     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1380198     Document Type: Article

References (23)

1. For palladium: Lyons T. W., Sanford M. S. Chem. Rev.: 2010; 110 1147
2. For rhodium: Colby D. A., Bergman R. G., Ellman J. A. Chem. Rev.: 2010; 110 624
3. For ruthenium: Arockiam P. B., Bruneau C., Dixneuf P. H. Chem. Rev.: 2012; 112 5879
4. Sui X., Zhu R., Gu Z. Synlett: 2013; 24 2023
5. Ferraccioli R. Synthesis: 2013; 45 581
6. Martins A., Mariampillai B., Lautens M. Top. Curr. Chem.: 2010; 292 1
7. Lautens M., Alberico D., Bressy C., Fang Y.-Q, Mariampillai B., Wilhelm T. Pure Appl. Chem.: 2006; 78 351
8. Weinstabl H., Suhartono M., Qureshi Z., Lautens M. Angew. Chem. Int. Ed.: 2013; 52 5305
9. Qureshi Z., Weinstabl H., Suhartono M., Lui H., Thesmar P., Lautens M. Eur. J. Org. Chem.: 2014; 4053
10. Sui X., Zhu R., Li G., Ma X., Gu Z. J. Am. Chem. Soc.: 2013; 135 9318
11. Catellani M., Cugini F. Tetrahedron: 1999; 55 6595
12. Catellani M., Motti E., Minari M. Chem. Commun.: 2000; 157
13. Rudolph A., Rackelmann N., Lautens M. Angew. Chem. Int. Ed.: 2007; 46 1485
14. Rudolph A., Rackelmann N., Turcotte-Savard M.-O, Lautens M. J. Org. Chem.: 2009; 74 289
15. Jutand A., Mosleh A. Organometallics: 1994; 14 1810
16. Amatore C., Carré E., Jutand A., M'Barki M. A. Organometallics: 1995; 14 1818
17. Catellani M., Fagnola M. C. Angew. Chem., Int. Ed. Engl.: 1994; 33 2421
18. Schaus S. E., Brandes B. D., Larrow J. F., Tokunaga M., Hansen K. B., Gould A. E., Furrow M. E., Jacobsen E. N. J. Am. Chem. Soc.: 2002; 124 1307
19. Santaniello E., Casati S., Ciuffreda P., Gamberoni L. Tetrahedron: Asymmetry: 2005; 16 1705
20. Appel R. Angew. Chem., Int. Ed. Engl.: 1975; 14 801
21. We attempted to determine the absolute stereochemistry of the alkylated product but all efforts gave crystals that were not suitable for X-ray crystal analysis. Use of the Mosher esters confirmed the ee but assigning the stereochemistry was not definitive. We anticipate overall inversion of 3m occurred, in analogy to our previous work, however we do not have definitive proof in this case. See the Supporting Information for analysis of the Mosher method.
22. Larchevêque M., Mambu L., Petit Y. Synth. Commun.: 1991; 21 2295
23. For a recent review of C-N coupling, see: Surry D. S., Buchwald S. L. Chem. Sci.: 2011; 2 27