Palladium-Catalyzed Synthesis of 1-Alkylidene-2-dialkylaminomethyl Cyclobutane Derivatives via Pd-Catalyzed Alkene Difunctionalization Reactions: Influence of Nucleophile and Water on the Reaction Mechanism

被引：2
作者：
Hatt, Jessica E. [1 ]
Shepich, James H. [1 ]
Clemons, Mackenzie N. [1 ]
Bornowski, Evan C. [1 ]
Wolfe, John P. [1 ]
机构：
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 18期
基金：
美国国家卫生研究院;
关键词：
REDUCTIVE ELIMINATION;
D O I：
10.1021/acs.orglett.3c00954
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pd-catalyzed coupling of 1,5-diene-2-yl triflates with amine nucleophiles affords exomethylenecyclobutanes bearing dialkylaminomethyl groups at C2. The strained carbocyclic products are obtained in moderate to excellent yields, with regioselectivities of up to >95:5 for four-membered ring formation. The mechanism of these reactions, which provides products resulting from anti-addition to alkenes, differs from related reactions involving malonate nucleophiles that provide syn-addition products.
引用
收藏
页码：3245 / 3248
页数：4
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