Literature DB >> 23544433

An efficient synthesis of fluorinated azaheterocycles by aminocyclization of alkenes.

Hai-Tsang Huang1, Tyler C Lacy, Barbara Błachut, Gerardo X Ortiz, Qiu Wang.   

Abstract

A general and efficient approach to important fluorinated azaheterocycles has been developed by incorporating nucleophilic fluorination into alkene difunctionalization. This intramolecular aminofluorination transformation of alkenes has been achieved via the aminocyclization of reactive unsaturated N-iodoamines, which can be generated in situ from either unsaturated N-chloramines or their amine precursors in a one-pot protocol.

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Year:  2013        PMID： 23544433     DOI： 10.1021/ol4003866

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


  10 in total

1.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

2.  Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.

Authors:  Brandon A Vara; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

3.  Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO2-Capture: Discovery, Development, and Mechanism.

Authors:  Roozbeh Yousefi; Thomas J Struble; Jenna L Payne; Mahesh Vishe; Nathan D Schley; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-12-24       Impact factor: 15.419

4.  Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.

Authors:  Charles E Hendrick; Stacey L McDonald; Qiu Wang
Journal:  Org Lett       Date:  2013-06-24       Impact factor: 6.005

5.  A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.

Authors:  Rene Ebule; Sagar Mudshinge; Michael H Nantz; Mark S Mashuta; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2019-02-27       Impact factor: 4.354

6.  Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.

Authors:  Ying He; Zhenyu Yang; Richard T Thornbury; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

7.  Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent.

Authors:  Weiming Yuan; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

8.  Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents.

Authors:  Kun Shen; Qiu Wang
Journal:  Chem Sci       Date:  2017-10-16       Impact factor: 9.825

Review 9.  Alkoxysulfenylation of alkenes: development and recent advances.

Authors:  Yan Cao; Somayeh Soleimani-Amiri; Roya Ahmadi; Alibek Issakhov; Abdol Ghaffar Ebadi; Esmail Vessally
Journal:  RSC Adv       Date:  2021-10-01       Impact factor: 4.036

10.  Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes.

Authors:  Zhishi Ye; Sarju Adhikari; Yu Xia; Mingji Dai
Journal:  Nat Commun       Date:  2018-02-19       Impact factor: 14.919
  10 in total

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