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Topic: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol  (Read 6654 times)

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Offline xyzi

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hi!

I'm looking for the mechanism of hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol (as solvent) but I've gone as far back as 1957 in the literature and can't find one.
Clayden showed a rough scheme but it has hydrogen gas as the H-donor.

I may just be missing it and I'd really appreciate it if somebody can point a reference to me (or better yet
suggest some steps..) 

thanks in advance.

Offline movies

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Re: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol
« Reply #1 on: September 27, 2007, 01:37:12 PM »
There is some evidence that it is a radical mechanism (at least for related reactions with Pd/C), but you could also draw it with Pd-hydrides.  You can inhibit the reaction by adding SET inhibitors, which points to radical intermediates.

see: Tetrahedron 2004, 7973.

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