Recent advances in transition-metal-catalyzed [2+2+2]-cyclo(co) trimerization reactions

Synthesis (Germany)

Volumn 44, Issue 17, 2012, Pages 2639-2672

  Broere, Daniël L J ^a   Ruijter, Eelco ^a  

^a AMSTERDAM INSTITUTE FOR MOLECULES   (Netherlands)

Author keywords

alkynes; cyclization; cycloaddition; homogeneous catalysis; transition metals

Indexed keywords

2-PYRIDONES; ALKYNES; ALTERNATIVE APPROACH; ATOM EFFICIENCY; BENZENE DERIVATIVES; CHEMO-SELECTIVITY; CHIRAL MOLECULE; CHIRAL SYSTEMS; CYCLIC MOLECULES; HOMOGENEOUS CATALYSIS; NATURAL PRODUCTS; PYRIDINE DERIVATIVES; PYRIDONES; REACTION PARTNERS; SINGLE-STEP; SUBSTITUTED BENZENES; TOTAL SYNTHESIS; TRIMERIZATION; DIRECTING GROUPS;

ACETYLENE; BENZENE; CATALYSIS; CYCLIZATION; CYCLOADDITION; MOLECULES; ORGANIC POLYMERS; PYRIDINE; REACTION KINETICS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL); TRANSITION METALS; BENZENE REFINING; CHEMICAL REACTIONS; METALS; STEREOCHEMISTRY;

STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

1,2 BIS(DIPENTAFLUOROPHENYLPHOSPHINO)ETHANE; 1,2 BIS(DIPHENYLPHOSPHINO)ETHANE; 2 PYRIDONE DERIVATIVE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; ELECTROPHILICITY; ENVIRONMENTAL TEMPERATURE; ISOMER; ISOMERIZATION; NUCLEOPHILICITY; OXIDATIVE COUPLING; REVIEW; STOICHIOMETRY; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS; TRANSITION METAL CATALYZED [2+2+2] CYCLOTRIMERIZATION REACTION;

EID: 84865447951     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316757     Document Type: Review

References (29)

1. Bertholet PE. M. C. R. Hebd. Seances Acad. Sci.: 1866; 63 515
2. Kotha S, Brahmachary E, Lahiri K. Eur. J. Org. Chem.: 2005; 4741
3. Reppe W, Schweckendiek WJ. Justus Liebigs Ann. Chem.: 1948; 560 104
4. Saito S, Yamamoto Y. Chem. Rev.: 2000; 100 2901
5. Yamamoto Y. Curr. Org. Chem.: 2005; 9 503
6. Zhou L, Li S, Kanno K, Takahashi T. Heterocycles: 2010; 80 725
7. Shibata K, Tanaka K. Synthesis: 2012; 44 323
8. Heller B, Hapke M. Chem. Soc. Rev.: 2007; 36 1085
9. Varela JA, Saá C. Chem. Rev.: 2003; 103 3787
10. Varela JA, Saá C. Synlett: 2008; 2571
11. This tutorial review focuses on stereoselectivity in higher-order carbocyclization reactions: Inglesby PA, Evans PA. Chem. Soc. Rev.: 2010; 39 2791
12. This highlight focuses on the most recent advances in solving the chemoselectivity: Galan BR, Rovis T. Angew. Chem. Int. Ed.: 2009; 48 2830
13. Shibata T, Tsuchikama K. Org. Biomol. Chem.: 2008; 6 1317
14. Tanaka K. Chem.-Asian J.: 2009; 4 508
15. Yamamoto Y, Ishii J, Nishiyama H, Itoh K. J. Am. Chem. Soc.: 2004; 126 3712
16. Yamamoto Y, Ishii J, Nishiyama H, Itoh K. J. Am. Chem. Soc.: 2005; 127 9625
17. Kotora M. Pure Appl. Chem.: 2010; 82 1813
18. Kadlčíková A, Hrdina R, Valterová I, Kotora M. Adv. Synth. Catal.: 2009; 351 1279
19. Yu RT, Rovis T. J. Am. Chem. Soc.: 2006; 128 2782
20. Yu RT, Rovis T. J. Am. Chem. Soc.: 2006; 128 12370
21. Lee EE, Rovis T. Org. Lett.: 2008; 10 1231
22. Yu RT, Rovis T. J. Am. Chem. Soc.: 2008; 130 326
23. Yu RT, Lee EE, Malik G, Rovis T. Angew. Chem. Int. Ed.: 2009; 48 2379
24. Keller Friedman R, Rovis T. J. Am. Chem. Soc.: 2009; 131 10775
25. Dalton DM, Oberg KM, Yu RT, Lee EE, Perreault S, Oinen ME, Pease ML, Malik G, Rovis T. J. Am. Chem. Soc.: 2009; 131 15717
26. Schmid R, Kirchner K. J. Org. Chem.: 2003; 68 8339
27. Dazinger G, Schmid R, Kirchner K. New J. Chem.: 2004; 28 153
28. Nicolaou KC, Tang Y, Wang J. Angew. Chem. Int. Ed.: 2009; 48 3449
29. The reported synthesis has also been the subject of a highlight: Li P, Menche D. Angew. Chem. Int. Ed.: 2009; 48 5078