Literature DB >> 11429858

The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.

H M Petrassi1, K B Sharpless, J W Kelly.   

Abstract

[figure: see text] A novel route to aryloxyamines via the copper-mediated cross-coupling of N-hydroxyphthalimide and phenylboronic acids is reported. The reaction is mediated by selected copper(I) and (II) salts in the presence of pyridine and is tolerant of several functional groups on the phenylboronic acid. The phthallmide group is removed using hydrazine to afford the corresponding aryloxyamine.

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Year:  2001        PMID: 11429858     DOI: 10.1021/ol0003533

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


  9 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors:  David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

3.  Pd-catalyzed O-arylation of ethyl acetohydroximate: synthesis of O-arylhydroxylamines and substituted benzofurans.

Authors:  Thomas J Maimone; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

4.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

5.  Tuning Sensory Properties of Triazole-Conjugated Spiropyrans: Metal-Ion Selectivity and Paper-Based Colorimetric Detection of Cyanide.

Authors:  Juhyen Lee; Eun Jung Choi; Inwon Kim; Minhe Lee; Chinnadurai Satheeshkumar; Changsik Song
Journal:  Sensors (Basel)       Date:  2017-08-07       Impact factor: 3.576

6.  A redox-neutral catechol synthesis.

Authors:  Qian Wu; Dingyuan Yan; Ying Chen; Ting Wang; Feng Xiong; Wei Wei; Yi Lu; Wei-Yin Sun; Jie Jack Li; Jing Zhao
Journal:  Nat Commun       Date:  2017-01-27       Impact factor: 14.919

7.  Copper(II)-mediated O-arylation of protected serines and threonines.

Authors:  Mirna El Khatib; Gary A Molander
Journal:  Org Lett       Date:  2014-09-10       Impact factor: 6.005

8.  Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

Authors:  Dimitra Kontokosta; Daniel S Mueller; Dong-Liang Mo; Wiktoria H Pace; Rachel A Simpson; Laura L Anderson
Journal:  Beilstein J Org Chem       Date:  2015-11-04       Impact factor: 2.883

9.  Microwave Application and Anhydrous Cu(OAc)2 Mediated O-Arylation of Aliphatic Amino Alcohols.

Authors:  Mohammad Al-Masum; Linda Quinones; Laurance T Cain
Journal:  Int J Org Chem (Irvine)       Date:  2016-05-27
  9 in total

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