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Improving C=N Bond Reductions with (Cyclopentadienone)iron Complexes: Scope and Limitations
Author(s) -
Cettolin Mattia,
Bai Xishan,
Lübken Dennis,
Gatti Marco,
Facchini Sofia Vailati,
Piarulli Umberto,
Pignataro Luca,
Gennari Cesare
Publication year - 2019
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.201801348
Subject(s) - chemistry , enantioselective synthesis , catalysis , reductive amination , aldimine , transfer hydrogenation , amination , combinatorial chemistry , scope (computer science) , double bond , stereochemistry , organic chemistry , computer science , programming language , ruthenium
Herein, we broaden the application scope of (cyclopentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre‐catalyst 1b , which is more active than the “Knölker complex” ( 1a ) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre‐isolated or generated in situ. The kinetics of 1b ‐promoted CTH of ketimine S1 were assessed, showing a pseudo‐first order profile, with TOF = 6.07 h –1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.