Revisiting Arene C(sp2 )-H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Angewandte Chemie
Yeongyu HwangSukbok Chang

Abstract

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C-H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

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Citations

Apr 23, 2021·Journal of the American Chemical Society·Euijae LeeSukbok Chang
Jul 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Changcheng JingJohn F Bower
May 5, 2021·Angewandte Chemie·Lauren G O'Neil, John F Bower
Aug 27, 2019·Journal of the American Chemical Society·Hoimin JungSukbok Chang
Aug 30, 2019·Journal of the American Chemical Society·Kaj M van VlietBas de Bruin
Apr 21, 2020·Journal of the American Chemical Society·Yeongyu HwangSukbok Chang
Feb 28, 2020·The Journal of Organic Chemistry·Jitian LiuXiaoxun Li
Jun 11, 2019·Journal of the American Chemical Society·Seung Youn Hong, Sukbok Chang
Jun 13, 2019·Journal of the American Chemical Society·Jin-Sheng YuMasakatsu Shibasaki
Dec 3, 2021·Chemical & Pharmaceutical Bulletin·Hidetoshi Noda
Jan 28, 2022·Organic Letters·Yu-Yong LuanYong-Min Liang

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