trans-Carbocarbonation of Internal Alkynes through a Formal anti-Carbopalladation/C-H Activation Cascade

Angewandte Chemie
Andreas RedingDaniel B Werz

Abstract

An intramolecular Pd-catalyzed cascade reaction is presented that consists of a formal anti-carbopalladation of a C-C triple bond followed by C-H activation. As a result, oligocyclic ring systems with an embedded tetrasubstituted double bond are formed. The key to success in affording the trans geometry of the emerging double bond are alkyne units with residues that must not undergo β-hydride elimination (e.g., t-butyl or silyl groups). Silyl groups proved to be a perfect handle to further convert the tetrasubstituted alkenes. The evaluation of kinetic data with a deuterium-labeled compound and X-ray analyses of trapped intermediates provided additional insight into the catalytic cycle.

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Citations

Jul 24, 2018·Chemistry : a European Journal·Theresa SchitterDaniel B Werz
Sep 6, 2018·Chemistry : a European Journal·Tapas Kumar AcharDebabrata Maiti
Jan 9, 2019·Chemical Communications : Chem Comm·Ryo ShintaniKyoko Nozaki
Jul 25, 2019·Angewandte Chemie·Kankanala RamakrishnaDebabrata Maiti
Feb 6, 2020·Angewandte Chemie·Benedikt S SchreibErick M Carreira
Sep 11, 2020·Angewandte Chemie·Zeqi JiangQing Xiao
Apr 23, 2020·The Journal of Organic Chemistry·Pratibha Chand-ThakuriMichael C Young
Jun 1, 2019·Journal of the American Chemical Society·Jinwon JeonSungwoo Hong
Nov 19, 2020·Journal of the American Chemical Society·Jinwon JeonSungwoo Hong
Apr 18, 2019·Organic Letters·Hongming Jin, Alois Fürstner
Oct 7, 2021·Chemistry : a European Journal·Finn J GeffersDaniel B Werz
Nov 5, 2021·Chemistry : a European Journal·Océane FloresJean Suffert
Jan 6, 2022·Chemistry : a European Journal·Simone M Gillbard, Hon Wai Lam

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