Literature DB >> 25942322

Oxidative inter-/intermolecular alkene diamination of hydroxy styrenes with electron-rich amines.

Michael W Danneman1, Ki Bum Hong1, Jeffrey N Johnston1.   

Abstract

Doubly intermolecular alkene diamination is achieved with electron-rich, terminal alkenes through the use of a hypervalent iodine (PhI(OAc)2) reagent, iodide, and electron-rich amines. Mono- and disubstituted amines combine with electron-rich alkenes, particularly o-hydroxystyrenes, to achieve the greatest level of generality. This operationally straightforward protocol, unreliant on conventional metal-based activation, is compatible with a broad range of functional groups.

Entities:  

Year:  2015        PMID: 25942322     DOI: 10.1021/acs.orglett.5b01177

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


  9 in total

1.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
Journal:  Org Lett       Date:  2016-10-25       Impact factor: 6.005

2.  Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams.

Authors:  John H Conway; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-12-26       Impact factor: 15.419

3.  Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.

Authors:  Kun Shen; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-09-05       Impact factor: 15.419

4.  Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

Authors:  Zainab M Khoder; Christina E Wong; Sherry R Chemler
Journal:  ACS Catal       Date:  2017-06-15       Impact factor: 13.084

5.  Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores.

Authors:  Sang Won Park; Soong-Hyun Kim; Jaeyoung Song; Ga Young Park; Darong Kim; Tae-Gyu Nam; Ki Bum Hong
Journal:  Beilstein J Org Chem       Date:  2018-05-11       Impact factor: 2.883

6.  The Synthesis of 2-Aminobenzoxazoles Using Reusable Ionic Liquid as a Green Catalyst under Mild Conditions.

Authors:  Ya Zhou; Zhiqing Liu; Tingting Yuan; Jianbin Huang; Chenjiang Liu
Journal:  Molecules       Date:  2017-04-02       Impact factor: 4.411

7.  Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.

Authors:  Jenna L Payne; Zihang Deng; Andrew L Flach; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2022-06-08       Impact factor: 9.969

8.  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

9.  Selenophosphoramide-catalyzed diamination and oxyamination of alkenes.

Authors:  John R Tabor; Derek C Obenschain; Forrest E Michael
Journal:  Chem Sci       Date:  2019-12-26       Impact factor: 9.825

  9 in total

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