NaHBEt₃-catalyzed HBpin hydroboration and deoxygenation of primary, secondary, and tertiary amides

Abstract

The reduction of amides to amines has always been a challenging and attractive process. Herein, we show that in the presence of NaHBEt3 acting as a catalyst, primary, secondary and...

Reduction of Amides to Amines Catalyzed by Ca(CH2C6H4NMe2‐o)2(THF)2/HBpin

“…Compared to hydrogenation and hydrosilylation approaches, deoxygenation of amides by hydroboration is a more effective procedure to obtain amines, in particular to reduce primary amides into amides [11] . Then, upon to date, catalysts suitable for hydroboration reactions such as POCN pincer Ni(II), [12] [(aNHC)‐KN(SiMe 3 )] 2 , [13] La 4 O(acac) 10 , [14] Cp* 2 ThMe 2 , [15] KO t Bu/BEt 3 , [16] (2,6‐di‐tert‐butylphenote)Li(THF), [17] La(CH 2 C 6 H 4 NMe 2 ‐o ) 3 @SBA‐15, [18] Ca[N(SiMe 3 ) 2 ](THF) 2 , [19] La(CH 2 C 6 H 4 NMe 2 ‐ o ) 3 , [20] Cp 2 ZrH 2 , [21] NaHBEt 3 , [22] and Eu 16 (tfac) 20 (CH 3 OH) 8 ( μ 3 ‐OH) 24 (μ 6 ‐O) 2 [23] are capable of mediating the transformation of all kinds of primary, secondary and tertiary amides into the corresponding amides. Therefore, to exploit efficient catalysts for the hydroborative reduction of amides to amines is still of great interest.…”