Pd-Catalyzed Domino Narasaka-Heck/C-H Activation/Amination Reactions: Synthesis of Bis-heterocyclic Spirocycles

被引：11

作者：

Bajohr, Jonathan ^{[1
]}

Dupeux, Aureïlien ^{[1
]}

Schenk, Daniel ^{[1
]}

Jans, Clara ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 28期

基金：

加拿大自然科学与工程研究理事会;

关键词：

N BOND FORMATION; ARYL IODIDES; ALKYLATION; AMINATION; CYCLIZATIONS; MECHANISM; ACCESS;

D O I：

10.1021/acs.orglett.3c01941

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thepalladium-catalyzed synthesis of bis-heterocyclic spirocyclescontaining both pyrroline and indoline motifs is reported. Di-tert-butyldiaziridinone is used to functionalize palladacyclesgenerated in situ via domino Narasaka-Heck/C-Hactivation reactions. The reaction is readily scalable, and the spirocyclicproducts can undergo deprotection, reduction, and (3 + 2) cycloadditions,highlighting their synthetic utility. Additionally, kinetic isotopeeffect experiments support a turnover-limiting C-H functionalizationstep in the catalytic cycle.

引用

页码：5361 / 5365

页数：5

共 42 条

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