Literature DB >> 23406020

Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO.

Soham Maity1, Srimanta Manna, Sujoy Rana, Togati Naveen, Arijit Mallick, Debabrata Maiti.   

Abstract

Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.

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Year:  2013        PMID: 23406020     DOI: 10.1021/ja311942e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

1.  Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

Authors:  Johnny W Lee; Sanghyun Lim; Daniel N Maienshein; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-24       Impact factor: 15.336

2.  Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation.

Authors:  Yue Xia; Nicholas W Wade; Philip N Palermo; Yidong Wang; Yi-Ming Wang
Journal:  Chem Commun (Camb)       Date:  2021-12-09       Impact factor: 6.222

3.  Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane.

Authors:  Philipp C Roosen; Alexander S Karns; Bryan D Ellis; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2022-01-06       Impact factor: 4.198

4.  Kinetically controlled E-selective catalytic olefin metathesis.

Authors:  Thach T Nguyen; Ming Joo Koh; Xiao Shen; Filippo Romiti; Richard R Schrock; Amir H Hoveyda
Journal:  Science       Date:  2016-04-29       Impact factor: 47.728

5.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236

6.  1,4-Addition of TMSCCl₃ to nitroalkenes: efficient reaction conditions and mechanistic understanding.

Authors:  Na Wu; Benoit Wahl; Simon Woodward; William Lewis
Journal:  Chemistry       Date:  2014-05-21       Impact factor: 5.236

7.  Selective Dealkenylative Functionalization of Styrenes via C-C Bond Cleavage.

Authors:  Jianzhong Liu; Jun Pan; Xiao Luo; Xu Qiu; Cheng Zhang; Ning Jiao
Journal:  Research (Wash D C)       Date:  2020-11-10

8.  Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.

Authors:  Xiao-Qiang Hu; Xiaotian Qi; Jia-Rong Chen; Quan-Qing Zhao; Qiang Wei; Yu Lan; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2016-04-06       Impact factor: 14.919

9.  Copper-catalyzed oxidative C(sp3)-H/C(sp2)-H cross-coupling en route to carbocyclic rings.

Authors:  Rui Wang; Yan Li; Ruo-Xing Jin; Xi-Sheng Wang
Journal:  Chem Sci       Date:  2017-03-15       Impact factor: 9.825

10.  Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles.

Authors:  Junting Chen; Jiakun Li; Matthew B Plutschack; Florian Berger; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

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