These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation
preprintrevised on 26.07.2019, 06:13 and posted on 26.07.2019, 16:03 by Alexandre Djurovic, Marie Vayer, Zhilong Li, Régis Guillot, Jean Pierre Baltaze, Vincent Gandon, Christophe Bour
We report a catalytic tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation. 1,4-Cyclohexadiene has been used as H2 surrogate to reduce the cyclic alkenes formed after the metathesis step. The same NHC-stabilized cationic gallium(III) complex, [IPr˙GaCl2][SbF6], performs the two steps with functional group tolerance. This reaction is stereoselective, leading either to 1,2-cisdisubstituted cyclopentanes or to a variety of cyclohexanes. DFT computations support an unexpected mechanism involving the activation of 1,4-cyclohexadiene by superelectrophilic gallium(III) dimers.
Ministère de lʼEnseignement supérieur, de la Recherche et de lʼInnovation (MESRI, PhD follows to A. Djurovic and M. Vayer
Université Paris Sud
Chinese Scholarship Council (CSC, PhD fellow to Z. Li)
Email Address of Submitting Authorchristophe.firstname.lastname@example.org
InstitutionUniversité Paris Sud
ORCID For Submitting Author0000-0001-6733-5284
Declaration of Conflict of Interestno conflict of interest
Read the published paper
in Organic Letters