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Chemoselective Kumada‐Type Iron Catalysis with Alkyl Grignard Reagents: Reductive Cyclization and Cyclomethylation
Author(s) -
Kim Jae Gon,
Baek Jong Hwa,
Kim Ye Ji,
Jang Yu Jeong,
Kang Eun Joo
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900359
Subject(s) - chemistry , alkyl , reagent , alkene , catalysis , organic chemistry , diene , reductive elimination , medicinal chemistry , combinatorial chemistry , natural rubber
A chemoselective reductive cyclization and cyclomethylation reaction of 7‐iodohept‐2‐yne and 7‐iodohepta‐1,2‐diene derivatives has been carried out using an iron catalyst and various alkyl Grignard reagents, resulting in the formation of pyrrolidines, tetrahydrofurans, and carbocycles with an alkene functional group. The reaction is initiated by single‐electron transfer from reduced Fe species to alkyl iodides and the resulting Fe−H or Fe−Me compound differentiated the structures of the cyclized products, which exhibited diverse complexities and synthetic utilities.