C-H bond functionalization via hydride transfer: Lewis acid catalyzed alkylation reactions by direct interamolecular coupling of sp 3 C-H bonds and reactive alkenyl oxocarbenium intermediates

Journal of the American Chemical Society

Volumn 131, Issue 2, 2009, Pages 402-403

  McQuaid, Kevin M ^a   Sames, Dalibor ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ALKYL ETHERS; ALKYLATION PRODUCTS; ALKYLATION REACTIONS; BIOLOGICALLY ACTIVE COMPOUNDS; BORON TRIFLUORIDE ETHERATE; C-H BOND; CARBONYL COMPOUNDS; CATALYTIC SYSTEM; CHEMICAL YIELDS; COMPLEX ORGANIC MOLECULES; DIASTEREO-SELECTIVITY; DIRECT COUPLING; FASTER RATES; FUNCTIONALIZATION; HYDRIDE TRANSFERS; IN-SITU FORMATIONS; LEWIS ACID; NEW APPROACHES; ORGANIC MATERIALS; ORGANOCATALYST; OXOCARBENIUM; ROOM TEMPERATURE; UNSATURATED ALDEHYDES; ZWITTERIONIC INTERMEDIATE;

ALDEHYDES; ALKYLATION; BORON; BORON COMPOUNDS; CARBONYLATION; CONDENSATION REACTIONS; CYCLIZATION; ETHERS; ETHYLENE; ETHYLENE GLYCOL; KETONES; SYNTHESIS (CHEMICAL); TRANSITION METALS;

ACTIVATED CARBON;

ALKENE; BORON TRIFLUORIDE; ETHYLENE GLYCOL; KETONE; LEWIS ACID; MENTHOL; TRANSITION ELEMENT; BORANE DERIVATIVE; BORON TRIFLUORIDE ETHERATE; ETHER DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIELS ALDER REACTION; STEREOCHEMISTRY; X RAY ANALYSIS; CHEMISTRY; SYNTHESIS;

ALKENES; ALKYLATION; BORANES; CYCLIZATION; ETHERS, CYCLIC; KETONES;

EID: 62849106266     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806068h     Document Type: Article

References (16)

1. (a) Godula, K.; Sames, D. Science 2006, 312. 67-72.
2. (b) Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422-6425.
3. (a) Kakiuchi. F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
4. (b) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556-6557.
5. (c) Shi, L.; Tu. Y.-Q.; Wang, M.; Zhang. F.-M.; Fan, C.-A.; Zhao, Y.-M.; Xia, W.-J. J. Am. Chem. Soc. 2005, 127, 10836-10837.
6. Pastine. S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005. 127, 12180-12181.
7. The tert-amino effect cyclizations: (a) Verboom, W.; Reinhoudt. D. N.; Visser, R.; Harkema, S. J. Org. Chem. 1984, 49, 269-276.
8. Recent review: (b)Mátyus, P.; Éliás, O.; Tapolcsányi, P.; Polonka-Bálint, A.; Halász-Dajka, B. Synthesis 2006, 16, 2625-2639.
9. Formation of carbocvcles: (c) Atkinson. R S.; Green, R. H. J. Chem. Soc., Perkin Tans. 1 1974, 394-401.
10. (a) Gassman, P. G.; Singleton. D. A.; Wilwerding. J. J.; Chavan, S. P. J . Am. Chem. Soc. 1987, 109, 2182-2184.
11. (b) Roush, W. R.; Gillis, H. R.; Essenfeld. A. P. J. Org. Chem. 1984. 49, 4674-4682.
12. Review: (c) Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371-2395.
13. For oxidative alkvlation of benzyl and allyl ethers using an external oxidant, see: Tu. W.; Liu, L.; Floreancig, P. E. Angew. Chem. Int. Ed. 2008, 47, 41844187.
14. For enantioselective hydride reduction of (α,β-unsaturated aldehydes and ketones using amine organocatalysts, see: (a) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32-33.
15. (b) Ouellet, S. G.; Walji, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327-1339.
16. Unfortunately, the amine organocatalysts were not able to catalyze the intramolecular alkvlation reactions discussed in this paper.