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Barry M. Trost
绿色化学领域的主要创始人、原子经济性概念的提出者、美国总统绿色化学挑战奖获得者
Ruthenium Catalyzed ReactionsRuthenium Catalyzed Reactions
Lu-Trost-Inoue Reaction
Tsuji-Trost AllylationTsuji-Trost Allylation
Dinuclear Zinc CatalystDinuclear Zinc Catalyst
Ruthenium Catalyzed ReactionsRuthenium Catalyzed Reactions
•extreme conditions
•lack of selectivity
•limitations in terms of reaction partner
Alder ene reaction
In 1990s, this reaction is atom-economic but was found minimal use because of :
First StepFirst Step
Ruthenium Catalysis: Mechanism Study
Chemoselectivity in the Ruthenium Catalyzed Redox Isomerization of Allyl Alcohols Trost, B.M.; Kulawiec, R.J. J. Am. Chem. Soc. (1993) 115 2027
Barry M. Trost,* F. Dean Toste, and Hong ShenJ. Am. Chem. Soc., 2000, 122 (10), pp 2379–2380
vinylcyclopropanesdiene-like
yne
diene 4+2
5+2
Paul A. Wender, J. Am. Chem. Soc., 1995, 117 (16), pp 4720–4721
Rh catalyzed 5+2 cycloaddition
Paul A. Wender,* J. Am. Chem. Soc., 1998, 120 (42), pp 10976–10977
Paul A. Wender, J. Am. Chem. Soc., 2006, 128 (19), pp 6302–6303
A Ruthenium-Catalyzed Hydrative Cyclization and[4 + 2] Cycloaddition of Yne-enones
R Au
HO
?
(a) CpRu(CH3CN)3PF6 (13 mol%), DCM, 34% (80% b.r.s.m.);(b) NBS, DMF, 98%; (c) CSA (10 mol%), CH3OH, 0 oC, 93–96%; Nature 456,485-488(2008)
Ru catalysed yne-enone coupling/Michael addition
Trost, B. M., Yang, H. & Wuitschik, G. A..Org. Lett. 7, 4761–4764 (2005).
Tsuji-Trost AllylationTsuji-Trost Allylation
Lu-Trost-Inoue Reaction
Barry M. Trost, Thomas. SchmidtJ. Am. Chem. Soc., 1988, 110 (7), pp 2301–2303X. Lu, Tetraderon Lett. 1988, 29,1045;
Lu-Trost-Inoue Reaction Trost reported in 1992 that triphenylphosphine alone catalyzes the transformation when warmed to 80 – 110oC in toluene
B. M. Trost, J. Am. Chem. Soc. 1992, 114,7933;X. Lu, Chem. Commun. 1993, 394;
PPh3 and acetic acid were necessary to isomerize alkynyl esters, whereas PPh3 alone was sufficient to isomerize the more reactivealkynyl ketones.
Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 3167.
Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670.
Addition of Oxygen Nucleophiles to 2-Alkynoates
Jianwei Sun and Gregory C. FuJ. Am. Chem. Soc., 2010, 132 (13), pp 4568–4569
Ying Kit Chung, Gregory C. Fu, 8, 12, 9, 2009, Pages: 2225-2227
Dinuclear Zinc CatalystDinuclear Zinc Catalyst
J. Am. Chem. Soc. 2006, 128, 8;
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