Continuous-flow transfer hydrogenation of benzonitrile using formate as a safe and sustainable source of hydrogen†
Seán D.
Dempsey, 
abc
Ailbhe A.
Ryan,
abc
Megan
Smyth,
b
Thomas S.
Moody,
bc
Andrew M.
Beale,
de
Sofia
Mediavilla Madrigal,
ef
Paul
Dingwall,
a
Peter C.
Knipe,
*a
Mark J.
Muldoon
*a
and
Jillian M.
Thompson
*a
abc
Ailbhe A.
Ryan,
abc
Megan
Smyth,
b
Thomas S.
Moody,
bc
Andrew M.
Beale,
de
Sofia
Mediavilla Madrigal,
ef
Paul
Dingwall,
a
Peter C.
Knipe,
*a
Mark J.
Muldoon
*a
and
Jillian M.
Thompson
*a
Abstract
The continuous catalytic transfer hydrogenation of benzonitrile to benzylamine is demonstrated using a palladium on carbon catalyst with triethylammonium formate as reducing agent. Solvent choice was critical in overcoming rapid catalyst deactivation. A 15-fold increase in catalyst productivity was observed in flow compared to batch, which was achieved using an ethanol–water solvent in combination with intermittent catalyst regeneration by washing with water.
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