钯催化烯烃氧化反应研究进展
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摘要
钯催化化学是金属有机化学的一个重要分支。钯催化剂是研究较早、应用较广泛的一类过渡金属催化剂。其中,钯催化烯烃氧化反应备受广大研究者的关注。本文着重综述了钯催化烯烃氧化反应的发展情况,以Wacker反应为主线进行分类归纳总结。文章还结合目前有机合成的前沿领域和现状,提出了目前钯催化烯烃氧化反应存在的问题和限制。最后,提出了钯催化烯烃氧化反应的研究前景和展望。
Palladium catalytic chemistry is an important branch of organometallic chemistry. Palladium catalyst is a kind of transition metal catalyst which has been studied earlier and widely used. In addition,palladium-catalyzed oxidation of olefins is concerned by many researchers. The development of palladium-catalyzed oxidation of olefins was reviewed with the Wacker reaction as the main line. The deficiencies and shortcomings of the reactions were also discussed in the light of the frontier fields and current situation of organic synthesis. Finally,the research prospects and expectation of palladium catalyzed oxidation of olefins were proposed.
Palladium catalytic chemistry is an important branch of organometallic chemistry. Palladium catalyst is a kind of transition metal catalyst which has been studied earlier and widely used. In addition,palladium-catalyzed oxidation of olefins is concerned by many researchers. The development of palladium-catalyzed oxidation of olefins was reviewed with the Wacker reaction as the main line. The deficiencies and shortcomings of the reactions were also discussed in the light of the frontier fields and current situation of organic synthesis. Finally,the research prospects and expectation of palladium catalyzed oxidation of olefins were proposed.
引文
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[2] Bckvall J E. Palladium in some selective oxidation reactions[J]. Acc.Chem. Res.,1983,16(9):335-342.
[3] Hamad O,Henry P M,Thompson C. Palladium(II)-catalyzed exchange and isomerization reactions. Exchange of chiral allyl alcohols with hydroxide,methoxide,and phenyl at high[Cl-]. Stereochemistry of the Wacker reaction[J]. J. Org. Chem.,1999,64(21):7745-7750.
[4] Crimmins M T,Brown B H. An intramolecular Diels-Alder approach to the eunicelins:Enantioselective total synthesis of ophirin B[J]. J.Am. Chem. Soc.,2004,126(33):10264-10266.
[5] Michel B W,Camelio A M,Cornell C N,et al. A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant:Application to classically challenging substrates[J]. J. Am.Chem. Soc.,2009,131(17):6076-6077.
[6] Michel B W,Steffens L D,Sigman M S. On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands[J]. J. Am.Chem. Soc.,2011,133(21):8317-8325.
[7] Weiner B,Baeza A,Jerphagnon T,et al. Aldehyde selective Wacker oxidations of phthalimide protected allylic amines:A new catalytic route toβ3-amino acids[J]. J. Am. Chem. Soc.,2009,131(27):9473-9474.
[8] Dong J J,Harvey E C,Fananas-Mastral M,et al. Palladiumcatalyzed anti-Markovnikov oxidation of allylic amides to protectedβ-amino aldehydes[J]. J. Am. Chem. Soc.,2014,136(49):17302-17307.
[9] Bckvall J E,Byetrm S E,Nordberg R E. Stereo-and regioselective palladium-catalyzed 1,4-diacetoxylation of 1,3-dienes[J]. J. Org.Chem.,1984,49(24):4619-4631.
[10] Zhang Y,Sigman M S. Palladium(Ⅱ)-catalyzed enantioselective aerobic dialkoxylation of 2-propenyl phenols:A pronounced effect of copper additives on enantioselectivity[J]. J. Am. Chem. Soc.,2007,129(11):3076-3077.
[11] Jensen K H,Pathak T P,Zhang Y,et al. Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation[J]. J. Am. Chem. Soc.,2009,131(47):17074-17075.
[2] Bckvall J E. Palladium in some selective oxidation reactions[J]. Acc.Chem. Res.,1983,16(9):335-342.
[3] Hamad O,Henry P M,Thompson C. Palladium(II)-catalyzed exchange and isomerization reactions. Exchange of chiral allyl alcohols with hydroxide,methoxide,and phenyl at high[Cl-]. Stereochemistry of the Wacker reaction[J]. J. Org. Chem.,1999,64(21):7745-7750.
[4] Crimmins M T,Brown B H. An intramolecular Diels-Alder approach to the eunicelins:Enantioselective total synthesis of ophirin B[J]. J.Am. Chem. Soc.,2004,126(33):10264-10266.
[5] Michel B W,Camelio A M,Cornell C N,et al. A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant:Application to classically challenging substrates[J]. J. Am.Chem. Soc.,2009,131(17):6076-6077.
[6] Michel B W,Steffens L D,Sigman M S. On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands[J]. J. Am.Chem. Soc.,2011,133(21):8317-8325.
[7] Weiner B,Baeza A,Jerphagnon T,et al. Aldehyde selective Wacker oxidations of phthalimide protected allylic amines:A new catalytic route toβ3-amino acids[J]. J. Am. Chem. Soc.,2009,131(27):9473-9474.
[8] Dong J J,Harvey E C,Fananas-Mastral M,et al. Palladiumcatalyzed anti-Markovnikov oxidation of allylic amides to protectedβ-amino aldehydes[J]. J. Am. Chem. Soc.,2014,136(49):17302-17307.
[9] Bckvall J E,Byetrm S E,Nordberg R E. Stereo-and regioselective palladium-catalyzed 1,4-diacetoxylation of 1,3-dienes[J]. J. Org.Chem.,1984,49(24):4619-4631.
[10] Zhang Y,Sigman M S. Palladium(Ⅱ)-catalyzed enantioselective aerobic dialkoxylation of 2-propenyl phenols:A pronounced effect of copper additives on enantioselectivity[J]. J. Am. Chem. Soc.,2007,129(11):3076-3077.
[11] Jensen K H,Pathak T P,Zhang Y,et al. Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation[J]. J. Am. Chem. Soc.,2009,131(47):17074-17075.