Literature DB >> 16173716

Intermolecular C-N addition of amides and S-N addition of sulfinamides to arynes.

Zhijian Liu1, Richard C Larock.   

Abstract

An efficient, mild, transition-metal-free method has been developed for the intermolecular C-N sigma-bond addition of amides and S-N sigma-bond addition of sulfinamides to arynes to form one C-C bond and one heteroatom-carbon bond in one step at room temperature. Evidence for a stepwise mechanism is provided.

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Year:  2005        PMID： 16173716     DOI： 10.1021/ja054079p

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


  23 in total

1.  Sulfonamide-Trapping Reactions of Thermally Generated Benzynes.

Authors:  Yuanxian Wang; Lianyou Zheng; Thomas R Hoye
Journal:  Org Lett       Date:  2018-11-05       Impact factor: 6.005

2.  Silylaryl Halides Can Replace Triflates as Aryne Precursors.

Authors:  Milad Mesgar; Olafs Daugulis
Journal:  Org Lett       Date:  2016-07-14       Impact factor: 6.005

3.  Intermolecular C-O addition of carboxylic acids to arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

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.  Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.

Authors:  Shilpa A Worlikar; Richard C Larock
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

6.  New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.

Authors:  Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2018-10-10       Impact factor: 15.419

7.  Intermolecular C-O Addition of Carboxylic Acids to Arynes: Synthesis of o-Hydroxyaryl Ketones, Xanthones, 4-Chromanones, and Flavones.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Tetrahedron       Date:  2013-02-04       Impact factor: 2.457

8.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

9.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

10.  Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Authors:  Feng Shi; Jesse P Waldo; Yu Chen; Richard C Larock
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005
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