Organocatalytic oxidative dimerization of alcohols to esters

Synlett

Volumn 23, Issue 15, 2012, Pages 2261-2265

  Abramovich, Adi ^a   Toledo, Hila ^a   Pisarevsky, Evgeni ^a   Szpilman, Alex M ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

alcohols; catalysis; dimerization; esters; oxidation

Indexed keywords

(TETRAHYDROFURAN 2 YL)METHYL TETRAHYDROFURAN 2 CARBOXYLIC ACID; 1,4 DIOXAN 2 ONE; 2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ACETIC ACID; 2 (BENZYLOXY)ETHYL 2 (BENZYLOXY)ACETATE; 2 BUTOXYETHYL 2 BUTOXYACETATE; 2 PHENOXYETHYL 2 PHENOXYACETATE; 2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL; 3 PHENYLPROPYL 3 PHENYLPROPANOIC ACID; [2,2 DIMETHYL 1,3 DIOXOLAN 4 YL]METHYL 2,2 DIMETHYL 1,3 DIOXOLANE 4 CARBOXYLIC ACID; ALCOHOL DERIVATIVE; CHEMICAL COMPOUND; CYCLOBUTYLMETHYL CYCLOBUTANECARBOXYLIC ACID; DECYL DECANOIC ACID; ESTER DERIVATIVE; HEXYL HEXANOIC ACID; TETRAHYDRO 2H PYRAN 2 ONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; OXIDATION;

EID: 84865049980     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317018     Document Type: Article

References (22)

1. Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem.: 2006; 4 2337
2. Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL Jr, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem.: 2007; 9 411
3. Yunker MB, Fraser-Reid B. J. Chem. Soc., Chem. Commun.: 1975; 61
4. Kajigaeshi S, Kawamukai H, Fujisaki S. Bull. Chem. Soc. Jpn.: 1989; 62 2585
5. Morimoto T, Hirano M, Hamaguchi T, Shimoyama M, Zhuang X. Bull. Chem. Soc. Jpn.: 1992; 65 703
6. Takase K, Masuda H, Kai O, Nishiyama Y, Sakagushi S, Ishii Y. Chem. Lett.: 1995; 871
7. Moria N, Togo H. Tetrahedron: 2005; 61 5915
8. Tumkevicius S, Navickas V, Dailide M. Pol. J. Chem.: 2006; 80 1377
9. Nikishin GI, Sokova LL, Kapustina NI. Russ. Chem. Bull., Int. Ed.: 2011; 60 310
10. Tamaru Y, Yamada Y, Inoue K, Yamamoto Y, Yoshida Z. J. Org. Chem.: 1983; 48 1286
11. Murahashi S.-I, Naota T, Ito K, Maeda Y, Taki H. J. Org. Chem.: 1987; 52 4319
12. Suzuki T, Matsuo T, Watanabe K, Katoh T. Synlett: 2005; 1453
13. Zhang J, Leitus G, Ben-David Y, Milstein D. J. Am. Chem. Soc.: 2005; 127 10840
14. Izumi A, Obora Y, Sakaguchi S, Ishii Y. Tetrahedron Lett.: 2006; 47 9199
15. Arita S, Koike T, Kayaki Y, Ikariya T. Chem. Asian J.: 2008; 3 1479
16. Musa S, Shaposhnikov I, Cohen S, Gelman D. Angew. Chem. Int. Ed.: 2011; 50 3533
17. Spasyuk D, Smith S, Gusev DG. Angew. Chem. Int. Ed.: 2012; 51 2772
18. Sheng X, Ma H, Gao J, Du Z, Xu J. Oxid. Commun.: 2010; 33 274
19. Liu X, Wu J, Shang Z. Synth. Commun.: 2012; 42 75
20. For an example of NHC-catalyzed synthesis of esters from allylic and benzylic alcohols, see: Maki BE, Chan A, Phillips EM, Scheidt KA. Org. Lett.: 2007; 9 371
21. Bobbitt JM, Brückner C, Merbouh N. Org. React. (NY): 2010; 74 103
22. Tebben L, Studer A. Angew. Chem. Int. Ed.: 2011; 50 5034