Charge migration in dicationic electrophiles and its application to the synthesis of aza-polycyclic aromatic compounds

Organic Letters
Ang LiDouglas A Klumpp

Abstract

[reaction: see text] Superacid-promoted reactions of dicationic electrophiles have been studied, and the positive charge centers are found to migrate apart in a predictable manner. Using isotopic labeling the charge migration is found in one system to occur through successive deprotonation-reprotonation steps. The charge migration chemistry is the basis for new general synthetic route to aza-polycyclic aromatic compounds.

Citations

Jul 4, 2013·Chemical Reviews·Rajasekhar Reddy Naredla, Douglas A Klumpp
Apr 23, 2011·Beilstein Journal of Organic Chemistry·Douglas A Klumpp
Dec 6, 2014·Mediators of Inflammation·M MachariaT E Matsha
Mar 13, 2018·Chemical Communications : Chem Comm·Rui-Qi LiTeck-Peng Loh
Feb 26, 2016·Chemical Communications : Chem Comm·Tanmay ChatterjeeEun Jin Cho
Oct 7, 2016·Chemical Communications : Chem Comm·Zhong ZhangPingfan Li
Jan 1, 2008·Chemistry : a European Journal·Douglas A Klumpp
Apr 2, 2019·Chemical Communications : Chem Comm·Wei-Bin LinChuan-Feng Chen
Apr 2, 2008·The Journal of Organic Chemistry·Ang LiDouglas A Klumpp
Feb 14, 2009·The Journal of Organic Chemistry·Matthew R SheetsDouglas A Klumpp
Apr 1, 2010·The Journal of Organic Chemistry·Haitao YuYan Zhang
Jan 22, 2008·Organic Letters·Cheng-Chieh Huang, Nein-Chen Chang
Mar 4, 2017·Organic Letters·Nicolas ProbstSébastien Thibaudeau

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