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Organic reactions catalyzed by 1, 4-diazabicyclo
[2.2.2] octane (DABCO)
- YANG Hua1, TIAN Rui1, LI Ye2
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1.College of Chemistry and Chemical Engineering, Yan''an University; 2.Yan'an Health School
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History
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Published |
05 Sep 2008 |
Issue Date |
05 Sep 2008 |
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References
1. Baylis A B Hillman M E D Offenlegungsschrift 2155113,1972; U.S. Patent 3,743,669Chem Abstr 1972 7734174q
2. Rafel S Leahy J W An unexpected rate acceleration-practicalimprovements in the Baylis-Hillman reactionJ Org Chem 1997 62(5)15211552. doi:10.1021/jo961224w
3. Kaye P T Nocanda X W Application of Baylis-Hillmanmethodology in a chemoselective synthesis of 3-acyl-2H-1-chromenesJChem Soc, Perkin Trans 2000 113311332. doi:10.1039/b001148g
4. Lee K Y Kim J M Kim J N Facile synthesis of 3-alkylidene-3H- isobenzofuranones from the Baylis-Hillman reactionof 2-carboxybenzaldehydeSynlett 2003 (3)357360
5. Faltin C Fleming E M Connon S J Acrylamide in the Baylis-Hillman reaction: expanded reactionscope and the unexpected superiority of DABCO over more basic tertiaryAmine catalystsJ Org Chem 2004 69(19)64966499. doi:10.1021/jo0490907
6. Kaye P T Nocanda X W A convenient general synthesisof 3-substituted 2H-chromene derivativesJ Chem Soc, Perkin Trans 2002 113181323. doi:10.1039/b201827f
7. Coelho F Almeida W P Veronese D Mateus C R Silva Lopes E C Rossi R C Silveira G P C Pavam C H Ultrasound in Baylis-Hillman reactionswith aliphatic and aromatic aldehydes: scope and limitationsTetrahedron 2002 58(37)74377447. doi:10.1016/S0040‐4020(02)00822‐0
8. De Souza R O M A Meireles B A Aguiar L C S Vasconcellos M L A A Hexamethylenetetramine as a cheap and convenient alternative catalystin the Baylis-Hillman reaction: synthesis of aromatic compounds withanti-malarial activitySynthesis 2004 (10)15951600
9. Areces P Carrasco E Mancha A Plumet J Tandem B-elimination-morita-Baylis-Hillman reaction in A,B-unsaturated sugar aldehydesSynthesis 2006 (6)946948
10. Shi M Li C Q Jiang J K Reexamination of the traditional Baylis-Hillman reactionTetrahedron 2003 59(8)11811189. doi:10.1016/S0040‐4020(03)00041‐3
11. Raheem I T Jacobsen E N Highly enantioselective aza-Baylis-Hillmanreactions catalyzed by chiral thiourea derivativesAdv Synth Catal 2005 34717011708. doi:10.1002/adsc.200505230
12. Drewes S E Emslie N D Karodia N Khan A A Facile diastereoselectivesynthesis of 2,6-dialkyl-5-methylene-1,3-dioxan-4-ones via A-activatedvinyl estersChem Ber 1990 12314471448. doi:10.1002/cber.19901230641
13. Matsuya Y Hayashi K Nemoto H A novel modified Baylis-Hillman reaction of propiolateJ Am Chem Soc 2003 125(3)646647. doi:10.1021/ja028312k
14. Shi M Zhao G L Aza-Baylis-Hillman reactionsof diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylatesand acrylonitrileTetrahedron 2004 60(9)20832089. doi:10.1016/j.tet.2003.12.059
15. Turki T Villiéras J Amri H An efficient synthesis of alkyl A-(hydroxymethyl)acrylatesinduced by DABCO in an aqueous mediumTetrahedronletters 2005 46(17)30713072. doi:10.1016/j.tetlet.2005.03.005
16. Saxena R Patra A Batra S An alternate route to substituted 1, 4-pentanedienes throughacetates of Baylis-Hillman adducts in aqueous mediumSynlett 2003 (10)14391442
17. Yu C Z Lin B Hu L Efficient Baylis-Hillman reaction using stoichiometricbase catalyst and an aqueous mediumJ OrgChem 2001 66(16)54135418. doi:10.1021/jo015628m
18. Papageorgiou C D Ley S V Gaunt M J Organic-catalyst-mediated cyclopropanation reactionAngew Chem Int Ed 2003 42(7)828831. doi:10.1002/anie.200390222
19. Bremeyer N Smith S C Ley S V Gaunt M J An intramolecularorganocatalytic cyclopropanation reactionAngew Chem 2004 11627352738. doi:10.1002/ange.200454007
20. Papageorgiou C D Cubillo de Dios MA Ley S V Gaunt M J Enantioselectiveorganocatalytic cyclopropanation via ammonium ylidesAngew Chem Int Ed 2004 4346414644. doi:10.1002/anie.200460234
21. Kimachi T Kinoshita H Kusaka K Takeuchi Y Aoe M Ju-ichi M The highly trans-selective darzens reaction via ammoniumylidesSynlett 2005 (5)842844
22. Zhao G L Shi M Aza-Baylis-Hillman reactionsof N-tosylated aldimines with activatedallenes and alkynes in the presence of various Lewis Base promotersJ Org Chem 2005 70(24)99759984. doi:10.1021/jo051763d
23. Yang Z J Fan M J Mu R Z Liu W M Liang Y M A facile synthesis of highly functionalizeddihydrofurans based on 1, 4-diazabicyclo[2.2.2]octane(DABCO) catalyzedreaction of halides with enones.Tetrahedron 2005 61(38)91409146. doi:10.1016/j.tet.2005.07.009
24. Shi L Han Y Yang Z J Liu W M Liang Y M Stereoselective synthesis of trans-B-substituted X-ferrocenyl-X-butyrolactonesvia ammonium ylidesSynthesis 2005 (17)28512856
25. Fan M J Yan Z Y Liu W M Liang Y M DABCO-Catalyzedreaction of A-halo carbonyl compounds with dimethyl acetylenedicarboxylate:a novel method for the preparation of polysubstituted furans and highlyfunctionalized 2H-pyransJ Org Chem 2005 70(20)82048207. doi:10.1021/jo050903g
26. Fan M J Guo L N Liu X Y Liu W M Liang Y M A mild, convenient and efficient single-stepmethod for the synthesis of polysubstituted furans via ammonium ylideroutesSynthesis 2005 (3)391396
27. Fan M J Li G Q Liang Y M DABCO catalyzed reaction of various nucleophiles with activatedalkynes leading to the formation of alkenoic acid esters, 1,4-dioxane,morpholine, and piperazinone derivativesTetrahedron 2006 62(29)67826791. doi:10.1016/j.tet.2006.04.100
28. Fan M J Li G Q Li L H Yang S D Liang Y M DABCO-Catalyzed reaction of phenols or1,2-diphenols with activated alkynes leading to the formation of alkenoicacid esters or 1,3-dioxole derivativesSynthesis 2006 (14)22862292
29. Shi Y L Shi M DABCO-Catalyzed reaction ofallenic esters and ketones with salicyl N-tosylimines: synthesis of highly functionalized chromenesOrg Lett 2005 7(14)30573060. doi:10.1021/ol051044l
30. Shi Y L Shi M Synthesis of substituted chromenesthrough the DABCO-Catalyzed reaction of but-3-yn-2-one and methylpropiolate with salicyl N-tosyliminesChem Eur J 2006 1233743378. doi:10.1002/chem.200501291
31. Li J H Liu W J DABCO as an inexpensive andhighly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-couplingreactionOrg Lett 2004 6(16)28092811. doi:10.1021/ol048907f
32. Li J H Hu X C Liang Y Xie Y X PEG-400 promotedPd(OAc)2/DABCO-catalyzed cross-coupling reactionsin aqueous mediaTetrahedron 2006 62(1)3138. doi:10.1016/j.tet.2005.09.138
33. Li J H Liu W J Xie Y X Recyclable and Reusable Pd(OAc)2/DABCO/PEG-400 system for Suzuki-Miyaura cross-coupling reactionJ Org Chem 2005 70(14)54095412. doi:10.1021/jo050353m
34. Li J H Wang D P CuI/DABCO-Catalyzed cross-couplingreactions of aryl halides with arylboronic acidsEur J Org Chem 2006 20632066
35. Li J H Liang Y Wang D P Liu W J Xie Y X Yin D L EfficientStille cross-coupling reaction catalyzed by the Pd(OAc)2/DABCO catalytic systemJOrg Chem 2005 70(7)28322834. doi:10.1021/jo048066q
36. Li J H Deng C L Liu W J Xie Y X Pd(OAc)2/DABCO as an inexpensive and efficient catalytic systemfor Hiyama cross-coupling reactions of aryl halides with aryltrimethoxysilanesSynthesis 2005 (18)30393044
37. Li J H Zhu Q M Xie Y X Pd(OAc)2/DABCO-catalyzed Suzuki-Miyauracross-coupling reaction in DMFTetrahedron 2006 62(47)1088810895. doi:10.1016/j.tet.2006.08.103
38. Xie Y X Li J H Yin D L Amines as the ligands for Palladium-catalyzed couplingreactionChinese Journal of Organic Chemistry 2006 26(8)11551163
39. Li J H Zhang X D Xie Y X Efficient and copper-free Pd(OAc)2/DABCO-catalyzed Sonogashira cross-coupling reactionSynthesis 2005 (5)804808
40. Li J H Wang D P Xie Y X Pd(OAc)2/DABCO as a highly activecatalytic system for the Heck reactionSynthesis 2005 (13)21932197
41. Li J H Wang D P Xie Y X CuI/DABCO as a highly active catalytic system for the Heck-typereactionTetrahedron letters 2005 46(30)49414944. doi:10.1016/j.tetlet.2005.05.106
42. Shieh W C Dell S Bach A Repič O Blacklock T J Dual nucleophilic catalysiswith DABCO for the N-methylation of IndolesJ Org Chem 2003 68(5)19541957. doi:10.1021/jo0266644
43. Shieh W C Lozanov M Loo M Repic O Blacklock T J DABCO-and DBU-accelerated greenchemistry for N-, O-, and S-benzylation with dibenzyl carbonateTetrahedronletters 2003 44(24)45634565. doi:10.1016/S0040‐4039(03)00992‐4
44. Lesch B Toräng J Vanderheiden S Bräse S Base-catalyzedcondensation of 2-hydroxybenzaldehydes with A,B-unsaturated aldehydes-scopeand limitationsAdv Synth Catal 2005 347555562. doi:10.1002/adsc.200404239
45. Sonye J P Koide K On the mechanism of DABCO-catalyzedisomerization of X-hydroxy-A,B-alkynoates to X-oxo-A, B-(E)-alkenoatesOrgLett 2006 8(2)199202. doi:10.1021/ol052376t
46. Sonye J P Koide K Base-catalyzed stereoselectiveisomerization of electron-deficient propargylic alcohols to E-enonesJ OrgChem 2006 71(16)62546257. doi:10.1021/jo060304p
47. Fioravanti S Colantoni D Pellacani L Tardella P A Aziridinesversus vinyl carbamates from the direct amination of electron-withdrawinggroup-substituted trifluoromethyl enoatesJ Org Chem 2005 70(8)32963298. doi:10.1021/jo050044w
48. Uozumi Y Arii T Watanabe T Double carbonylation of aryl iodides with primary aminesunder atmospheric pressure conditions using the Pd/PPh3/DABCO/THF systemJ Org Chem 2001 66(15)52725247. doi:10.1021/jo0156924
49. Shi Y J Humphrey G Maligres P E Reamer R A Michael Williams J Highly regioselective DABCO-catalyzednucleophilic aromatic substitution reaction of methyl 2,6-dichloronicotinatewith phenolsAdv Synth Catal 2006 348309312. doi:10.1002/adsc.200505431