Palladium(I) Dimer Enabled Extremely Rapid and Chemoselective Alkylation of Aryl Bromides over Triflates and Chlorides in Air

Angewandte Chemie
Indrek KalvetFranziska Schoenebeck

Abstract

Disclosed herein is the first general chemo- and site-selective alkylation of C-Br bonds in the presence of COTf, C-Cl and other potentially reactive functional groups, using the air-, moisture-, and thermally stable dinuclear PdI catalyst, [Pd(μ-I)PtBu3 ]2 . The bromo-selectivity is independent of the substrate and the relative positioning of the competing reaction sites, and as such fully predictable. Primary and secondary alkyl chains were introduced with extremely high speed (<5 min reaction time) at room temperature and under open-flask reaction conditions.

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Sep 24, 2014·The Journal of Organic Chemistry·Indrek KalvetFranziska Schoenebeck
Jun 30, 2015·Angewandte Chemie·Marialuisa AufieroFranziska Schoenebeck
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May 14, 2016·Accounts of Chemical Research·Theresa SpergerFranziska Schoenebeck
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Citations

Feb 22, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Kent O KirlikovaliAlexander M Spokoyny
May 23, 2018·Angewandte Chemie·Matthew J O'NeillJosep Cornella
Nov 2, 2018·Angewandte Chemie·Claudia J DiehlFranziska Schoenebeck
Oct 18, 2018·Chemistry : a European Journal·Yantao Chen
Feb 6, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Michelle MontgomeryRobin B Bedford
Mar 29, 2019·Chemistry : a European Journal·Simon WagschalLaurence Grimaud
Mar 27, 2019·Chemistry : a European Journal·Erdem SenolFranziska Schoenebeck
Apr 16, 2020·Angewandte Chemie·Samir Bouayad-GervaisFranziska Schoenebeck
Jul 14, 2020·Angewandte Chemie·Christoph FrickeFranziska Schoenebeck
Oct 23, 2018·Angewandte Chemie·Theresa SpergerFranziska Schoenebeck
Jun 14, 2019·Angewandte Chemie·Xiang-Yu ChenFranziska Schoenebeck
Jul 30, 2020·Angewandte Chemie·Viktoria H GessnerIlja Rodstein
Oct 16, 2020·Angewandte Chemie·Christoph FrickeFranziska Schoenebeck
Nov 19, 2020·Chemistry : a European Journal·Emily K ReevesSharon R Neufeldt
May 25, 2021·Journal of the American Chemical Society·Beatrice LansbergenTobias Ritter
Apr 7, 2020·Journal of the American Chemical Society·Amit DahiyaFranziska Schoenebeck
Jun 4, 2020·Organic Letters·Aymane SelmaniFranziska Schoenebeck
Sep 28, 2021·Accounts of Chemical Research·Christopher Uyeda, Conner M Farley
Dec 11, 2021·The Journal of Organic Chemistry·Chathurika R K JayasundaraRobert E Maleczka

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