Literature DB >> 21417453

Palladium-catalyzed C-CN activation for intramolecular cyanoesterification of alkynes.

Naveen R Rondla1, Samuel M Levi, Jonathan M Ryss, Rachel A Vanden Berg, Christopher J Douglas.   

Abstract

Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 21417453     DOI： 10.1021/ol200274h

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


  8 in total

1.  Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors:  Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
Journal:  Chem Commun (Camb)       Date:  2014-08-18       Impact factor: 6.222

Review 2.  Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

Authors:  Lifen Peng; Zhifang Hu; Hong Wang; Li Wu; Yinchun Jiao; Zilong Tang; Xinhua Xu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

3.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

4.  Transformations of X (C, O, N)-CN Bonds: Cases of Selective X (C, O, N)-C Activation.

Authors:  Rui Wang; John Russell Falck
Journal:  RSC Adv       Date:  2014-01-01       Impact factor: 3.361

5.  Synthesis and applications of rhodacyclopentanones derived from C-C bond activation.

Authors:  Megan H Shaw; John F Bower
Journal:  Chem Commun (Camb)       Date:  2016-07-07       Impact factor: 6.222

6.  Metal-Free Direct C-H Cyanation of Alkenes.

Authors:  Xi Wang; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-06       Impact factor: 15.336

7.  Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches.

Authors:  Xiao-Yu Miao; Yong-Ji Hu; Fu-Rao Liu; Yuan-Yuan Sun; Die Sun; An-Xin Wu; Yan-Ping Zhu
Journal:  Molecules       Date:  2022-09-27       Impact factor: 4.927

8.  Rh-Catalyzed Decarbonylation of Conjugated Ynones via Carbon-Alkyne Bond Activation: Reaction Scope and Mechanistic Exploration via DFT Calculations.

Authors:  Alpay Dermenci; Rachel E Whittaker; Yang Gao; Faben A Cruz; Zhi-Xiang Yu; Guangbin Dong
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825
  8 in total

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