Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions†,Organic Chemistry Frontiers

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Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-06-15 00:00:00 , DOI: 10.1039/c8qo00470f
Saswata Gupta _{1,

2,

3,

4} , Peipei Xie _{5,

6,

7,

8} , Yuanzhi Xia _{5,

6,

7,

8} , Daesung Lee _{1,

2,

3,

4}

Affiliation

The selectivity between two different manifolds of reactions of arynes reacting with functionalized alkenes is described. Arynes generated from bis-1,3-diynes react with various trisubstituted and 1,1-disubstituted alkenes including methallyl amine, prenyl azide, and methacrylic acid, providing mainly addition products of the polar heteroatom functionalities over the Alder-ene products of the alkene segment. The selectivity, however, intricately depends on the substituent pattern of the alkene. Except for the most reactive 2-propenyl group-containing aldehyde, α,β-unsaturated aldehydes generally participated in an addition reaction, generating chromene derivatives.

中文翻译：

芳烃对官能化烯烃的反应性：分子间的Alder-ene与加成反应†

描述了芳烃与官能化烯烃的反应的两个不同歧管之间的选择性。由双1,3-二炔生成的芳烃与各种三取代和1,1-二取代的烯烃（包括甲基烯丙基胺，异戊烯基叠氮化物和甲基丙烯酸）反应，主要提供极性杂原子官能度的加成产物，而不是烯烃的Alder-ene产物。分割。然而，选择性复杂地取决于烯烃的取代基图案。除了最具反应性的含2-丙烯基的醛外，α，β-不饱和醛通常参与加成反应，生成苯并二氢萘衍生物。

更新日期：2018-06-15

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