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Direct Hydrosilylation of Tertiary Amides to Amines by an In Situ Formed Iron/N‐Heterocyclic Carbene Catalyst
Author(s) -
Volkov Alexey,
Buitrago Elina,
Adolfsson Hans
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300010
Subject(s) - chemistry , hydrosilylation , carbene , catalysis , chemoselectivity , trifluoromethanesulfonate , organic chemistry , benzoyl chloride , silane , medicinal chemistry , in situ , polymer chemistry
Tertiary amides were efficiently reduced to their corresponding tertiary amines in high isolated yields by using the commercially available and inexpensive polymeric silane polymethylhydrosiloxane (PMHS) as the reducing agent. The reaction is efficiently catalyzed by an in situ generated iron/N‐heterocyclic carbene complex (1 mol‐%) obtained from iron(II) acetate and 1‐(2‐hydroxy‐2‐phenylethyl)‐3‐methylimidazolium triflate ([PhHEMIM][OTF]). A catalytic amount of lithium chloride (1 mol‐%) present in the reaction mixture significantly reduced the reaction time and increased the chemoselectivity of the reduction process.