Literature DB >> 26585593

An Exclusively trans-Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst.

Christine M Le1, Xiao Hou1, Theresa Sperger2, Franziska Schoenebeck3, Mark Lautens4.   

Abstract

Pharmaceutically relevant methylene oxindoles are synthesized by a palladium(0)-catalyzed intramolecular chlorocarbamoylation reaction of alkynes. A relatively underexplored class of caged phosphine ligands is uniquely suited for this transformation, enabling high levels of reactivity and exquisite trans selectivity. This report entails the first transition-metal-catalyzed atom-economic addition of a carbamoyl chloride across an alkyne.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chlorocarbamoylation; cyclization; homogenous catalysis; palladium; phosphaadamantane

Year:  2015        PMID： 26585593     DOI： 10.1002/anie.201507883

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

2.  Mechanistic insights on the Pd-catalyzed addition of C-X bonds across alkynes - a combined experimental and computational study.

Authors:  Theresa Sperger; Christine M Le; Mark Lautens; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2017-01-27       Impact factor: 9.825

3.  Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones.

Authors:  Valeria Nori; Antonio Arcadi; Armando Carlone; Fabio Marinelli; Marco Chiarini
Journal:  Beilstein J Org Chem       Date:  2020-05-20       Impact factor: 2.883

4.  Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C-C Cleavage of Cyclobutanols.

Authors:  Marta Pérez-Gómez; Piedad Herrera-Ramírez; Delia Bautista; Isabel Saura-Llamas; José-Antonio García-López
Journal:  Organometallics       Date:  2022-03-03       Impact factor: 3.876

5.  Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki-Miyaura cross-coupling reactions.

Authors:  Jairus L Lamola; Paseka T Moshapo; Cedric W Holzapfel; Munaka Christopher Maumela
Journal:  RSC Adv       Date:  2021-08-05       Impact factor: 4.036

6.  The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones.

Authors:  Ya-Fei Han; Gui-Fen Lv; Yang Li; Li-Jun Wu; Xuan-Hui Ouyang; Jin-Heng Li
Journal:  Chem Sci       Date:  2022-07-27       Impact factor: 9.969

7.  Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp3)-H Functionalization Cascades.

Authors:  Changcheng Jing; Benjamin T Jones; Ross J Adams; John F Bower
Journal:  J Am Chem Soc       Date:  2022-09-09       Impact factor: 16.383

8.  Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates.

Authors:  Ian R Hazelden; Rafaela C Carmona; Thomas Langer; Paul G Pringle; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-22       Impact factor: 15.336
  8 in total

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