Journal
TETRAHEDRON
Volume 95, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132339
Keywords
C-H functionalization; Alkylation; Pyridine; Bimetallic catalysis
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Funding
- JST CREST program [JPMJCR14L3]
- JSPS KAKENHI [JP20H00376]
- Japan Society for the Promotion of Science (JSPS)
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This study reports a C2-and mono-selective alkylation of various pyridines and azines with unactivated alkenes and vinylarenes using a heterobimetallic Rh-Al catalyst. Experimental results show that the use of aliphatic alkenes exclusively affords linear alkylation products, while vinylarenes mainly afford branched alkylation products. The details of the reaction mechanism, revealed by DFT calculations, indicate that the reductive elimination of the products is rate-determining, consistent with experimental results. The origin of the linear/branched selectivity is elucidated based on deformation/interaction analysis.
A C2-and mono-selective alkylation of various pyridines and azines with unactivated alkenes and vinylarenes using a heterobimetallic Rh-Al catalyst is reported. The use of aliphatic alkenes exclusively affords the linear alkylation products, while vinylarenes mainly afford branched alkylation products. The details of the reaction mechanism are revealed by DFT calculations: the reductive elimination of the products is rate-determining, which is consistent with the experimental results. The origin of the linear/ branched selectivity is elucidated based on deformation/interaction analysis. (c) 2021 Elsevier Ltd. All rights reserved.
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