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Synthesis and hydrolysis of [alkenyl(alkoxy)carbene]manganese complexes: Evidence for a transient allylic intermediate on the way to alpha,beta-unsaturated aldehydes
A variety of alkenylcarbene complexes [Cp'(CO)2Mn= C(OEt)CH=CHR] (3) (Cp’ = TiS-MeCsH4) was obtained in a straightforward manner upon aldol condensation of [Cp'(CO)2Mn=C(OEt)CH3] (1) with aromatic and alpha,beta- unsaturated aldehydes RC(H)O (2). The reaction is totally stereoselective, giving (E)- or (all-E)-alkenylcarbenes only. The protonation of 3 at low temperature followed by reaction with water affords the alpha,beta-unsaturated aldehyde complexes [Cp'(CO)2Mn(n2-RCH=CHCHO] (5), from which the aldehydes RC(H)=C(H)C(H)O (6) were displaced by acetonitrile. The intermediate aldehyde complexes are shown to result from the hydrolysis of a transient cationic pi- allyl species [Cp'(CO)2Mn(n3-RCHCHC(OEt)H]+ ([4]+) formed upon protonation of 3.
Synthesis and hydrolysis of [alkenyl(alkoxy)carbene]manganese complexes: Evidence for a transient allylic intermediate on the way to alpha,beta-unsaturated aldehydes
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Reference£º
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion