Literature DB >> 20738146

Palladium-catalyzed alkoxyamination of alkenes with use of N-fluorobenzenesulfonimide as oxidant.

Dmitry V Liskin1, Paul A Sibbald, Carolyn F Rosewall, Forrest E Michael.   

Abstract

A Pd-catalyzed alkoxyamination of protected aminoalkenes promoted by N-fluorobenzenesulfonimide is described. This mild transformation allows the direct formation of ethers from carbon-carbon double bonds. An unusual switch from exo to endo selectivity in polar solvents was discovered, allowing the selective formation of either regioisomer by careful choice of reaction conditions.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20738146     DOI： 10.1021/jo101171g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

Authors:  Osvaldo Gutierrez; Jason G Harrison; Ryan J Felix; Fernando Cortés Guzman; Michel R Gagné; Dean J Tantillo
Journal:  Chem Sci       Date:  2013-10       Impact factor: 9.825

2.  Steric Crowding Makes Challenging C(sp3)-F Reductive Eliminations Feasible.

Authors:  Shu-Bin Zhao; Jennifer J Becker; Michel R Gagné
Journal:  Organometallics       Date:  2011-08-08       Impact factor: 3.876

3.  Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

Authors:  Zachary K Wickens; Pablo E Guzmán; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

4.  Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.

Authors:  Monissa C Paderes; Sherry R Chemler
Journal:  European J Org Chem       Date:  2011-07-01

5.  Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

Authors:  Jiaming Li; Robert H Grubbs; Brian M Stoltz
Journal:  Org Lett       Date:  2016-10-18       Impact factor: 6.005

6.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

7.  Catalytic platinum-initiated cation-olefin reactions with alkene terminating groups.

Authors:  Joseph G Sokol; Nikki A Cochrane; Jennifer J Becker; Michel R Gagné
Journal:  Chem Commun (Camb)       Date:  2013-04-26       Impact factor: 6.222

8.  Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes.

Authors:  Hao Wang; Cui Chen; Weibing Liu; Zhibo Zhu
Journal:  Beilstein J Org Chem       Date:  2017-09-28       Impact factor: 2.883

9.  Anion-Dependent Switch in C-X Reductive Elimination Diastereoselectivity.

Authors:  Michael J Geier; Marzieh Dadkhah Aseman; Michel R Gagné
Journal:  Organometallics       Date:  2014-08-14       Impact factor: 3.876
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.