Literature DB >> 27978695

Pd-Catalyzed Spirocyclization via C-H Activation and Benzyne Insertion.

Hyung Yoon1, Alexis Lossouarn1, Felicitas Landau1, Mark Lautens1.   

Abstract

A palladium-catalyzed spirocyclization forming spirooxindoles and spirodihydrobenzofurans has been achieved. Mechanistic studies suggest that the transformation proceeds through sequential carbopalladation, C-H activation, and benzyne insertion. Both classes of spirocycles have been synthesized in good to excellent yields, and the procedure is readily scalable.

Entities:  

Year:  2016        PMID： 27978695     DOI： 10.1021/acs.orglett.6b03213

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Regioselective synthesis of spirocyclic pyrrolines via a palladium-catalyzed Narasaka-Heck/C-H activation/[4 + 2] annulation cascade reaction.

Authors:  Wan-Xu Wei; Xiangtao Kong; Rui-Qiang Jiao; Xue-Song Li; Cui-Tian Wang; Yuke Li; Yong-Min Liang
Journal:  Chem Sci       Date:  2022-05-06       Impact factor: 9.969

2.  Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study.

Authors:  Ivan Franzoni; Hyung Yoon; José-Antonio García-López; Amalia Isabel Poblador-Bahamonde; Mark Lautens
Journal:  Chem Sci       Date:  2017-12-08       Impact factor: 9.825

Review 3.  Transition metal-catalyzed synthesis of spirooxindoles.

Authors:  P V Saranya; Mohan Neetha; Thaipparambil Aneeja; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

4.  Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction.

Authors:  Hui-Xuan Chen; Yaqi Zhang; Yuyang Zhang; Xuefeng He; Zhen-Wei Zhang; Hao Liang; Wenhuan He; Xiaoding Jiang; Xiangmeng Chen; Liqin Qiu
Journal:  RSC Adv       Date:  2018-11-01       Impact factor: 4.036

5.  Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Authors:  Shuai Yang; Yanghui Zhang
Journal:  Molecules       Date:  2021-12-10       Impact factor: 4.411
  5 in total

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