Trapping Reactions of Benzynes Initiated by Intramolecular Nucleophilic Addition of a Carbonyl Oxygen to the Electrophilic Aryne
作者:Bhavani Shankar Chinta、Sahil Arora、Thomas R. Hoye
DOI:10.1021/acs.orglett.1c04110
日期:2022.1.14
We describe here reactions in which a carbonyl oxygen atom initiates cascade reactions by nucleophilic attack on a covalently attached benzyne. The benzynes are produced by thermal cyclization of triynes via hexadehydro-Diels–Alder reaction. The initially produced oxocarbenium/aryl carbanionic zwitterion is protonated in situ by an external protic nucleophile (NuH) of appropriate acidity. The resulting
我们在这里描述了羰基氧原子通过对共价连接的苯进行亲核攻击而引发级联反应的反应。苯炔是通过六氢-Diels-Alder 反应通过三炔的热环化产生的。最初产生的氧碳正离子/芳基碳负离子两性离子被适当酸度的外部质子亲核试剂 (NuH) 原位质子化。由此产生的离子对 (oxocarbenium + /Nu – ) 通过几个不同的机械流形崩溃,增加了可以生成的结构类别的多样性。