Concepedia

Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides

Nuligonda Thirupathi, Madala Hari Babu, Vikas Dwivedi, Ruchir Kant, Maddi Sridhar Reddy

Organic Letters · 2014 · 87 citations · 37 references

DOI

Concepts

Abstract

A novel palladium-catalyzed approach to 2-benzofuranyl/indolylacetamides from 1-(o-hydroxy/aminophenyl)propargylic alcohols and isocyanides is described. The reaction proceeds through a cascade that includes oxy/aminopalladation, isocyanide insertion, and 1,4-hydroxyl migration. No oxidant or ligand is needed to promote the cascade, and the reactions are carried out under mild conditions to afford the products through high functional tolerance.

References

37

Palladium‐Catalyzed Migratory Insertion of Isocyanides: An Emerging Platform in Cross‐Coupling Chemistry

Tjøstil Vlaar, Eelco Ruijter, Bert U. W. Maes et al. · Angewandte Chemie International Edition · 2013 · 427 citations

, , +11

A Simple and Efficient Approach to the Synthesis of 2-Phenylquinazolines via sp<sup>3</sup> C−H Functionalization

Jintang Zhang, Dapeng Zhu, Chenmin Yu et al. · Organic Letters · 2010 · 217 citations

, , +5

Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp<sup>3</sup>)–H Activation: Concise Synthesis of Indole Derivatives

Takeshi Nanjo, Chihiro Tsukano, Yoshiji Takemoto · Organic Letters · 2012 · 188 citations

, , +17

Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides

Huanfeng Jiang, Bifu Liu, Yibiao Li et al. · Organic Letters · 2011 · 185 citations

, , +12

A palladium-catalyzed three-component reaction for the preparation of quinazolin-4(3H)-imines

Guanyinsheng Qiu, Gang Liu, Shouzhi Pu et al. · Chemical Communications · 2012 · 121 citations

, , +8