The heck reaction applied to 1,3- and 1,2-unsaturated derivatives, a way towards molecular complexity

Molecules

Volumn 15, Issue 4, 2010, Pages 2667-2685

  Deagostino, Annamaria ^a   Prandi, Cristina ^a   Tabasso, Silvia ^a   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

1,2 dienes; 1,3 dienes; Mizoroki Heck reaction; Palladium

Indexed keywords

ALKADIENE; ALLENE; BIOLOGICAL PRODUCT; PALLADIUM;

CATALYSIS; CHEMISTRY; CYCLIZATION; REVIEW; SYNTHESIS;

ALKADIENES; BIOLOGICAL PRODUCTS; CATALYSIS; CYCLIZATION; PALLADIUM;

EID: 77951851867     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15042667     Document Type: Review

References (39)

1. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Chichester, UK, 2004.
2. Heck, R.F. Organic Reactions; John Wiley and Sons: Chichester, UK, 1982; Volume 27, 356-358.
3. Grigg, R.; Sridharan, V.; Sukirthalingam, S.; Worakun, T. Regiospecific palladium catalysed tandem cyclisation-anion capture processes. Carbon-, nitrogen- and oxygen-centred nucleophiles. Tetrahedron Lett. 1989, 30, 1139-1142.
4. Grigg, R.; Brown, S.; Sridahan, V.; Uttley, M.D. Intermolecular Heck-Diels-Alder Cascade Processes of Alkylallenes. Tetrahedron Lett. 1998, 39, 3247-3250. (Pubitemid 28198001)
5. Larock, R.C.; Tu, C.; Pace, P. Synthesis of medium-ring nitrogen heterocycles via palladiumcatalyzed heteroannulation of 1,2-dienes. J. Org. Chem. 1998, 63, 6859-6866. (Pubitemid 128719238)
6. Larock, R.C.; He, Y.; Leong, W.W.; Han, X.; Refvik, M.D.; Zenner, J.M. Palladium-catalyzed annulation of allenes using functionally substituted vinylic halides. J. Org. Chem. 1998, 63, 2154-2160. (Pubitemid 128494202)
7. Larock, R.C.; Berriospena, N.G.; Fried, C.A. Regioselective, Palladium-catalyzed heteroannulation and carboannulation of 1,2-Dienes using functionally substituted aryl halides. J. Org. Chem. 1991, 56, 2615-2617.
8. Larock, R.C. Palladium-catalyzed annulation. J. Organom. Chem. 1999, 576, 111-124.
9. Zenner, J.M.; Larock, R.C. Palladium-catalyzed, asymmetric hetero- and carboannulation of allenes using functionally-substituted aryl and vinylic iodides. J. Org. Chem. 1999, 64, 7312-7322. (Pubitemid 29477629)
10. Ma, S.; Negishi, E.I. Palladium-Catalyzed Cyclization of .omega.-Haloallenes. A New General Route to Common, Medium, and Large Ring Compounds via Cyclic Carbopalladation. J. Am. Chem. Soc. 1995, 117, 6345-6357.
11. Ma, S.; Zhao, S. Pd(0)-Catalyzed Insertionâ'Cyclization Reaction of 2,3-Allenols with Aryl or Alkenyl Halides. Diastereoselective Synthesis of Highly Optically Active trans-2,3-Disubstituted Vinylic Oxiranes. J. Am. Chem. Soc. 1999, 121, 7943-7944. (Pubitemid 29420520)
12. Deagostino, A.; Prandi, C.; Venturello, P. Palladium-catalyzed heck reaction on 1-alkoxy-1,3dienes: A regioselective gamma-arylation of alpha,beta-unsaturated carbonyl compounds. Org. Lett. 2003, 5, 3815-3817. (Pubitemid 37412140)
13. Deagostino, A.; Migliardi, M.; Occhiato, E.G.; Prandi, C.; Zavattaro, C.; Venturello, P. LIC-KOR promoted formation of conjugated dienes as useful building blocks for palladium-catalyzed syntheses. Tetrahedron 2005, 61, 3429-3436. (Pubitemid 40349276)
14. Beccaria, L.; Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. Heck reaction on 1-alkoxy1,3-dienes in ionic liquids: A superior medium for the regioselective arylation of the conjugated dienic system. Synlett 2006, 18, 2989-2992. (Pubitemid 44799988)
15. Lyapkalo, I. M.; Webel, M.; Reißig, H.-U. Synthesis and Heck Reactions of Ethenyl- and (Z)Butadien-1-yl Nonaflate Obtained by the Fragmentation of Furan Derivatives. Eur. J. Org. Chem. 2001, 4189-4194. (Pubitemid 33081317)
16. 3: PalladiumCatalyzed Coupling Reactions of (η4-Chlorodiene)tricarbonyliron Complexeses. Organometallics 2006, 26, 223-229.
17. Deagostino, A.; Prandi, C.; Toppino, A.; Venturello, P. Palladium-catalysed Heck reaction on 1,2dien-1-ols: a stereoselective synthesis of alpha-arylated alpha,beta-unsaturated aldehydes. Tetrahedron 2008, 64, 10344-10349.
18. Gai, X.; Grigg, R.; Ramzan, M.I.; Sridharan, V.; Collard, S.; Muir, J.E. Pyrazole and benzothiazole palladacycles: stable and efficient catalysts for carbon-carbon bond formation. Chem. Commun. 2000, 2053-2054.
19. Evans, P.; Hogg, P.; Grigg, R.; Nurnabi, M.; Hinsley, J.; Sridharan, V.; Suganthan, S.; Korn, S.; Collard, S.; Muir, J.E. 8-Methylquinoline palladacycles: stable and efficient catalysts for carboncarbon bond formation. Tetrahedron 2005, 61, 9696-9704. (Pubitemid 41262046)
20. Grigg, R.; Koppen, I.; Rasparini, M.; Sridharan, V. Synthesis of spiro- and fused heterocycles by palladium catalysed carbo- and heteroannulation cascades of allenes. Chem. Commun. 2001, 11, 964-965. (Pubitemid 32521818)
21. Brown, S.; Grigg, R.; Hinsley, J.; Korn, S.; Sridharan, V.; Uttley, M.D. Three-component HeckDiels-Alder cascade processes involving alkylallenes, aryl iodides and dienophiles. Tetrahedron 2001, 57, 10347-10355. (Pubitemid 34008634)
22. Cooper, I.R.; Grigg, R.; MacLachlan, W.S.; Thornton-Pett, M.; Sridharan, V. 3-Component palladium-indium mediated diastereoselective cascade allylation of imines with allenes and aryl iodides. Chem. Commun. 2002, 13, 1372-1373. (Pubitemid 34651809)
23. Grigg, R.; Martin, W.; Morris, J.; Sridharan, V. Four-component Pd-catalysed cascade/ring closing metathesis. Synthesis of heterocyclic enones. Tetrahedron 2005, 61, 11380-11392.
24. Knoke, M.; de Meijere, A. Cyclopropyl building blocks in organic synthesis, part 85. A versatile access to 1-cyclopropyl-2-aryl-1,3,5-hexatrienes - Domino Heck-Diels-Alder reactions of 1,3dicyclopropyl-1,2-propadiene. Synlett 2003, 2, 195-198.
25. Knoke, M.; de Meijere, A. Domino Heck-Diels-Alder reactions of differently substituted cyclopropylallenes. Eur. J. Org. Chem. 2005, 11, 2259-2268. (Pubitemid 40830733)
26. Lu, G.L.; Malinakova, H.C. Regio- and diastereoselective insertion of allenes into stable oxapalladacycles with a metal-bonded stereogenic carbon. Preparation of contiguously substituted 3,4-dihydro-2H-1-benzopyrans. J. Org. Chem. 2004, 69, 8266-8279.
27. Hershberger, J.C.; Zhang, L.; Lu, G.L.; Malinakova, H.C. Polymer-supported palladacycles: Efficient reagents for synthesis of Benzopyrans with palladium recovery. Relationship among resin loading, Pd : P ratio, and reactivity of immobilized palladacycles. J. Org. Chem. 2006, 71, 231-235. (Pubitemid 43128080)
28. Inamoto, K.; Yamamoto, A.; Ohsawa, K.; Hiroya, K.; Sakamoto, T. Highly regioselective palladium-catalyzed annulation reactions of heteroatom- substituted allenes for synthesis of condensed heterocycles. Chem. Pharm. Bull. 2005, 53, 1502-1507. (Pubitemid 41634228)
29. Fu, C.L.; Ma, S.M. Observation of the first Heck-type cross-coupling reaction of allenes with aryl halides. Synthesis of polysubstituted 1,2-allenyl sulfones. Org. Lett. 2005, 7, 1605-1607.
30. Yu, F.; Lian, X.; Ma, S. Pd-Catalyzed Regio- and Stereoselective Cyclization-Heck Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids with Alkenes. Org. Lett. 2007, 9, 1703-1706.
31. Shu, W.; Yu, Q.; Ma, S. Development of a New Spiro-BOX Ligand and Its Application in Highly Enantioselective Palladium-Catalyzed Cyclization of 2-Iodoanilines with Allenes. Adv. Synth. Catal. 2009, 351, 2807-2810.
32. Fuwa, H.; Sasaki, M. A new method for the generation of indole-2,3-quinodimethanes and 2-(Nalkoxycarbonylamino)1,3-dienes. Intramolecular Heck/Diels-Alder cycloaddition cascade starting from acyclic -phosphono enecarbamates. Chem. Commun. 2007, 2876-2878. (Pubitemid 47035565)
33. Fuwa, H.; Tako, T.; Ebine, M.; Sasaki, M. A New Method for the Generation of Indole-2,3quinodimethane from Allenamides. Chem. Lett. 2008, 37, 904-905.
34. Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group. Org. Lett. 2008, 10, 5239-5242.
35. Beccalli, E.M.; Broggini, G.; Clerici, F.; Galli, S.; Kammerer, C.; Rigamonti, M.; Sottocornola, S. Palladium-Catalyzed Domino Carbopalladation/5- exo-Allylic Amination of (±)-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones. Org. Lett. 2009, 11, 1563-1566.
36. Imoto, J.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Palladium-Catalyzed 1-Methylene2-propenylation Reactions of Aryl Bromides with 3,4-Alkadien-1-ols via Carbon-Carbon Bond Cleavage for the Synthesis of 2-Aryl-1,3-butadiene Derivatives. Bull. Chem. Soc. Jpn. 2009, 82, 393-400.
37. Kammerer, C.; Prestat, G.; Madec, D.; Poli, G. Phosphine-Free Palladium-Catalyzed Allene Carbopalladation/Allylic Alkylation Domino Sequence: A New Route to 4-(alpha-Styryl) gammaLactams. Chem. Eur. J. 2009, 15, 4224-4227.
38. Chakravarty, M.; Kumara Swamy, K.C. Palladium-Catalyzed Coupling of Allenylphosphonates, Phenylallenes, and Allenyl Esters:  Remarkable Salt Effect and Routes to Novel Benzofurans and Isocoumarins. J. Org. Chem. 2006, 71, 9128-9138. (Pubitemid 44845742)
39. Pavan, M.P.; Manab, C.; Swamy, K.C.K. Pd-Catalyzed Reactions of Allenylphosphonates and Related Allenes with Functionalized 2-Iodophenols, 2-Iodobenzoic Acid, and 2-Iodobenzyl Alcohol Leading to Functionalized Benzofurans, Isocoumarins, and Benzopyrans. Eur. J. Org. Chem. 2009, 5927-5940.