Highly selective catalytic synthesis of (E, E)-1,4-diiodobuta-1,3-diene via atom-efficient addition of acetylene and iodine: A versatile (E, E)-1,3-diene building block in cross-coupling reactions

Synlett

Volumn , Issue 14, 2011, Pages 2021-2024

  Ananikov, Valentine P ^a   Kashin, Alexey S ^a   Hazipov, Oleg V ^a,b   Beletskaya, Irina P ^c   Starikova, Zoya A ^d  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b L M LITVINENKO INSTITUTE OF PHYSICAL ORGANIC AND COAL CHEMISTRY   (Ukraine)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

^d A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

cross coupling; green chemistry; natural product synthesis; Pt catalyst; total synthesis

Indexed keywords

1,3 DIENE; 1,4 DIIODOBUTA 1,3 DIENE; ACETYLENE; CHEMICAL COMPOUND; IODINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DEIODINATION; DIMERIZATION; ISOMERIZATION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; NUCLEOPHILICITY; PHOTOCHEMISTRY; PURIFICATION; ROOM TEMPERATURE; SOLUBILITY; SYNTHESIS; THERMODYNAMICS;

EID: 80052076923     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261166     Document Type: Article

References (30)

1. Metal-Catalyzed Cross-Coupling Reactions Diederich F Stang P J. Wiley-VCH Weinheim 2004
2. Beller M, Bolm C, Transition Metals for Organic Chemistry Wiley-VCH Weinheim 1998
3. Cross-Coupling Reactions: A Practical Guide, In Topics in Current Chemistry Vol. 219 Miyaura N Springer Heidelberg 2002
4. Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E John Wiley and Sons New York / Chichester 2002
5. Nolan S P., Navarro O, C-C Bond Formation by Cross-Coupling, In Comprehensive Organometallic Chemistry III Vol. 11 Mingos D M. P. Crabtree R H. Elsevier Oxford 2007 1-37
6. Chinchilla R, Nájera C, Chem. Rev. 2007 107 874
7. Corbet J.-P, Mignani G, Chem. Rev. 2006 106 2651
8. Schlummer B, Scholz U, Adv. Synth. Catal. 2004 346 1599
9. Classics in Total Synthesis II Nicolaou K C. Snyder S A. Wiley-VCH Weinheim 2003
10. Classics in Total Synthesis Nicolaou K C. Sorensen E J. Wiley-VCH Weinheim 1996
11. Chemler S R., Trauner D, Danishefsky S J., Angew. Chem. Int. Ed. 2001 40 4544
12. Pattenden G, Sinclair D J., J. Organomet. Chem. 2002 653 261
13. Nicolaou K C., Bulger P G., Sarlah D, Angew. Chem. Int. Ed. 2005 44 4442
14. Hong B.-C, Nimje R Y., Curr. Org. Chem. 2006 10 2191
15. Sasaki M, Bull. Chem. Soc. Jpn. 2007 80 856
16. Negishi E.-i, Bull. Chem. Soc. Jpn. 2007 80 233
17. Denmark S E., Liu J H.-C, Angew. Chem. Int. Ed. 2010 49 2978
18. Ananikov V P., Hazipov O V., Beletskaya I P., Chem. Asian J. 2011 6 306
19. The Chemistry of Dienes and Polyenes Rappoport Z John Wiley and Sons Chichester 1997
20. Mitchenko S A., Ananikov V P., Beletskaya I P., Ustynyuk Y A., Mendeleev Commun. 1997 130
21. Ananikov V P., Mitchenko S A., Beletskaya I P., Russ. J. Org. Chem. 2002 38 636
22. Ananikov V P., Mitchenko S A., Beletskaya I P., Nefedov S E., Eremenko I L., Inorg. Chem. Commun. 1998 1 411
23. Ananikov V P., Musaev D G., Morokuma K, Organometallics 2001 20 1652
24. Ananikov V P., Musaev D G., Morokuma K, Organometallics 2005 24 715
25. Babudri F, Farinola G M., Naso F, Ragni R, Spina G, Synthesis 2007 3088
26. Trostyanskaya I G., Titskiy D Y., Anufrieva E A., Borisenko A A., Kazankova M A., Beletskaya I P., Russ. Chem. Bull. Int. Ed. 2001 50 2095
27. Trostyanskaya I G., Maslova E N., Kazankova M A., Beletskaya I P., Russ. J. Org. Chem. 2008 44 24
28. Quesada E, Acuña A U., Amat-Guerri F, Angew. Chem. Int. Ed. 2001 40 2095
29. Serebryakov E P., Vasilev A A., Titskii D Y., Beletskaya I P., Mendeleev Commun. 2000 10 168
30. Gung B W., Omollo A O., Eur. J. Org. Chem. 2009 1136