Directed Ortho Metalation

Directed Ortho Metalation - Myers Review: Snieckus, V....

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DMG RLi Ar N O R R O Ar N CH 3 CH 3 O P ArO NR 2 NR 2 ArOCH 2 OCH 3 ArF ArCl S t -Bu Ar O O ArOCH 3 ArO N O R R Ar N DMG Li ArN O -Bu O – ArCH 2 N(CH 3 ) 2 ArCF 3 ArO – N N R R Ar NR 2 Ar O – H ArN(CH 3 ) 2 Ar OR OR Ar N O – R DMG E ArOCH 2 OCH 3 O Ar N CH 3 CH 3 Ar OR OR CONR CONR 2 > > SO 2 NR 2 , SO 2 NR, CH 2 NR 2 , OCH 3 , Cl NR 2 Ar O – H O Ar N CH 3 CH 3 Myers Review: Snieckus, V. Chem. Rev. 1990 , 879. • Directed metalation of anisole with n -BuLi was discovered independently in 1939-1940 by Gilman and Wittig. This led to the discovery of more than 40 directing groups. Gilman, H.; Bebb, R. L. J. Am. Chem. Soc. 1939 , 61 , 109. Wittig, G.; Fuhrman, G. Chem. Ber. 1940 , 73 , 1197. SO 2 NR 2 , CONR, CH 2 NR 2 > OCH 3 > CH 2 CH 2 NR 2 , CF 3 , F, NR 2 Slocum, D. W.; Jennings, C. A. J. Org. Chem. 1976 , 41 , 3653. • Protective groups that also serve as strong directing groups are especially useful: Directed Ortho Metalation Chem 215 Beak, P.; Brown, R. A. 1982
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Directed Ortho Metalation - Myers Review: Snieckus, V....

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