Literature DB >> 20397661

Combined directed ortho metalation-halogen dance (HD) synthetic strategies. HD-anionic ortho fries rearrangement and double HD sequences.

Ricarda E Miller1, Toni Rantanen, Kevin A Ogilvie, Ulrich Groth, Victor Snieckus.   

Abstract

A general and efficient directed ortho metalation (DoM)-halogen dance (HD)-electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines. Furthermore, a hitherto unobserved double HD rearrangement is reported. Under similar LDA conditions, aromatic O-carbamates with OMe, Cl, and F substituents (4a-c) undergo either a HD-electrophile quench sequence, 4a-c --> 18-20, or a HD-anionic ortho Fries rearrangement, 4a-c --> 6a-c, respectively.

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Year:  2010        PMID： 20397661     DOI： 10.1021/ol100493v

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


  5 in total

1.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

2.  On the control of secondary carbanion structure utilising ligand effects during directed metallation.

Authors:  Andrew E H Wheatley; Jonathan Clayden; Ian H Hillier; Alison Campbell Smith; Mark A Vincent; Laurence J Taylor; Joanna Haywood
Journal:  Beilstein J Org Chem       Date:  2012-01-09       Impact factor: 2.883

3.  Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate.

Authors:  Tao Liu; Xiaoxue Yuan; Gang Zhang; Yi Zeng; Tong Chen; Gongying Wang
Journal:  RSC Adv       Date:  2019-09-06       Impact factor: 4.036

4.  Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement.

Authors:  Jessica Matthias; Thines Kanagasundaram; Klaus Kopka; Carsten S Kramer
Journal:  Beilstein J Org Chem       Date:  2019-10-01       Impact factor: 2.883

5.  Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions.

Authors:  Claudia Feberero; Cintia Virumbrales; Carlos Sedano; Lorena Renedo; Samuel Suárez-Pantiga; Roberto Sanz
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411
  5 in total

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