Ag(I)催化的 N-对甲苯磺酰基氮丙啶和 N-对甲苯磺酰基氮杂环丁烷与 S、O 和 N 亲核试剂以及桥连双亲核试剂的区域选择性开环反应。
Ag(I)-catalyzed regioselective ring-opening of N-tosylaziridine and N-tosylazetidine with S-, O-, and N-nucleophiles and tethered dinucleophiles.
机构信息
Organometallics & Catalysis Laboratory, Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India.
出版信息
J Org Chem. 2011 Mar 4;76(5):1475-8. doi: 10.1021/jo102285z. Epub 2011 Feb 3.
PMID:21291173
Abstract
[Ag(COD)(2)]PF(6) catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).
摘要
[Ag(COD)(2)]PF(6) 能够催化 N-对甲苯磺酰基氮丙啶和氮杂环丁烷与醇、胺、硫醇和相关的 1,2-乙烷双亲核试剂的开环反应。初始速率研究和基于密度泛函理论的逐步能量评估表明，杂原子给体的亲核反应性与其与阳离子 Ag(I) 的结合亲和力之间呈反比关系。
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