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1、.1金属氢化物的还原及机理-NaBH4制作：小鱼爱大海.2一：金属氢化物还原反应官能团生成官能团LiAlH4NaBH4酮仲醇醛伯醇酯伯醇羧酸伯醇酰氯醛注：表示官能团能被还原；表示官能团不能被还原或反应很慢两种主要金属氢化物的还原特性1参考文献：1 闻韧 主编 药物合成反应 北京：化学工业出版社，2002.363.3还原试剂（金属氢化物）的选择：NaBH4 R CO2EtROHLiAlH4结论：反应迅速，但后处理操作复杂。.4二、文献查阅：NaBH4参与的还原反应CO2EtR4R1R2R3R4R1R2R3OHNaBH4(6.0 eq),MeOH(8mL)THF,70,2.0-4.0 h 88-9
2、7（一）、酯的还原1R1,R2,R3,R4:H,Cl,Br,F,OMeCO2RXXOHNaBH4/ZnCl2tertiary amine,THF,2hR=Me,EtX=2-Br,2-SCH2Ph,4-NO2,4-OH52-982Reference:1 Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;2 R.E.Ten-Brintk,
3、J.Org.Chem.1987,52,418;.5二、文献查阅：NaBH4参与的还原反应CO2EtNaBH4-I2THF,70,0.5 hH2OOH85（一）、酯的还原3Reference:3Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;4 R.Shundo,Y.Matsubara,K.Nishiguchi,T.Hirashima
4、,Bull.Chem.Soc.Jpn.65(1992)530;（二）羧酸的还原R-COOHROHNaBH4-ZnCl2THF,R=alkyl/aryl70-954.6二、文献查阅：NaBH4参与的反应（二）羧酸的还原5COOHOHNaBH4-ZrCl4THF,rt,5h856COOHOHNaBH4-I2THF,0-2582CO2EtCO2EtCH3(CH2)8COOHNaBH4-I2THF,0-25CH3(CH2)8CH2OH95Reference:5(a)S.Baskaran,V.Gupta,N.Chidambaram,S.Chandrasekaran,J.Chem.Soc.Commun.(
5、1989)903;(b)6 Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;.7二、文献查阅：NaBH4参与的还原反应RCOOHH2NRH2NOH80-98NaBH4/H2SO4,THFMeOH,NaOH（三）氨基酸及其衍生物的还原89RCOOHH2NRH2NOH45-94NaBH4-I2,THFrefluxR=alkyl or a
6、rylKOHMeOH8 9(a)Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;(b)R.P.McGeary,Tetrahedron Lett.39(1998)3319;.8二、文献查阅：NaBH4参与的还原反应PhCH2CNPhCH2CH2NH291NaBH4-ZrCl4THF,rt（四）氰基的还原PhCNNaBH4-I2THFN
7、aOHPhCH2NH272Reference:10 (a)Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;(b)T.Yamakawa,M Masaki,H.Nohira,Bull.Chem.Soc.Jpn.64(1991)2730;(c)C.F.Lane,Chem.Rev.76(1976)773;10.9二、文献查阅：NaBH4参与
8、的还原反应（五）酰氯的还原RCOClRCH2OHR=alkyl/aryl86-98 NaBH4-ZnCl2TMEDAReference:11Nubia Boechat,Jorge Carlos da Costa,Jorge de Souza Mendonca,Pedro Santos Mello de Oliveira and MarcusVinicius De Souza.Tetrahedron Letters 2004,45,6021-6022;.10四、氢负离子还原机理BHHHH+RRORCHOBH3RRCHOHR机理1、RCRONa BH3H+RCROBH3HNaRCRORCROBH2HRCRHORCRORCROR2HCOBOCHR2OCHR2OCHR2NaH2OHRCROHH4B(OH)3NaOH+机理：机理2、.11Thanks
硼氢化钠的还原及相关机理课堂PPT
