Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand

A highly efficient catalyst for Pd-catalyzed cyclopropanation was developed using a bulkier N-heterocyclic carbene ligand, with which the nitriles reacted with mono substituted allyl reagents to afford cyclopropanes in high yields with high cyclopropanation/allylation and enantioselectivities. The r...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 45; pp. 6449 - 6452
Main Authors Zhang, Gao-Peng, Huang, Shuai, Jiang, Yang-Jie, Liu, Xiu-Yan, Ding, Chang-Hua, Wei, Yin, Hou, Xue-Long
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 30.05.2019
Royal Society of Chemistry
Subjects
Allyl compounds
Carbonates
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Crystallography
Enantiomers
Ligands
Nitriles
NMR
Nuclear magnetic resonance
Organic compounds
Palladium
Physical Sciences
Reagents
Science & Technology
Substitutes
KETENE SILYL ACETAL
KETONES
LACTAM
ACYCLIC AMIDES
REAGENTS
MECHANISM
ASYMMETRIC CYCLOPROPANATION
(PI-ALLYL)PALLADIUM COMPLEXES
PI-ACCEPTOR PROPERTIES
NUCLEOPHILIC-ATTACK
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Summary:A highly efficient catalyst for Pd-catalyzed cyclopropanation was developed using a bulkier N-heterocyclic carbene ligand, with which the nitriles reacted with mono substituted allyl reagents to afford cyclopropanes in high yields with high cyclopropanation/allylation and enantioselectivities. The reasons for cyclopropanation were investigated and the usefulness of the products was demonstrated. Enantioselective cyclopropanation of nitriles with allyl reagents was realized using Pd/NHC as a catalyst and the reasons for the cyclopropanation were investigated.
Bibliography:CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
1856997
10.1039/c9cc01960j
Electronic supplementary information (ESI) available: Screening data, experimental procedures, NMR and HPLC spectra. Cif file of compound
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ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc01960j