Regioselectivity Differentiation in Metalations of 3,5-Dichloro-Tertiary versus Secondary Benzamides  

作　　者：Francesca Khani Tina Fleming Carleton Collins Erica Tabakin Lynn M. Bradley David A. Hunt Francesca Khani;Tina Fleming;Carleton Collins;Erica Tabakin;Lynn M. Bradley;David A. Hunt(Department of Chemistry, The College of New Jersey, Ewing, USA)

机构地区：[1]Department of Chemistry, The College of New Jersey, Ewing, USA

出　　处：《International Journal of Organic Chemistry》2016年第2期142-146,共5页有机化学国际期刊（英文）

摘　　要：Metalation regioslectivity of 3,5-dichlorobenzamides is a function of the type of amide (secondary versus tertiary) used in the sequence. Metalation at the 2-position (adjacent to the carboxamide functional group) occurs when the secondary benzamide is metalated with sec-butyllithium/ TMEDA mediated through complex-induced proximity effects (CIPE) process, whereas metalation with sec-butyllithium/TMEDA occurs exclusively at the 4-position when the tertiary benzamide is used under identical reaction conditions.Metalation regioslectivity of 3,5-dichlorobenzamides is a function of the type of amide (secondary versus tertiary) used in the sequence. Metalation at the 2-position (adjacent to the carboxamide functional group) occurs when the secondary benzamide is metalated with sec-butyllithium/ TMEDA mediated through complex-induced proximity effects (CIPE) process, whereas metalation with sec-butyllithium/TMEDA occurs exclusively at the 4-position when the tertiary benzamide is used under identical reaction conditions.

关 键 词：Directed Ortho-Metalation Complex-Induced Proximity Effects (CIPE) 3 5-Dichlorobenzamides 

分 类 号：O62[理学—有机化学]