Yawn. Reactions are stirring for the next two days… all hot plates are in use, what to do? READ THE LITERATURE OF COURSE!
I’m the worlds biggest fan of green chemistry. Not only because I *heart* the planet but because the reactions are so wonderfully simple. So, I bring you Ramesh Chandra’s Green Chem. (2006, 8, 519-521). Chandra’s found a new way to make benzadiazepines (not to be confused with the much more fun benzodiazepines). The reaction is elegantly simple and very high yeilding. Yields range anywhere for fantastic (84% for naphthaline derivative) to un-friggin-believable (99% for acetone). The mechanism is purported to go through this imine-enamine tautomerization stabilized by the silver. Attack is then done on the imine carbon for the coup de grâce. If
you’re wondering if this works on cyclic systems then you should wonder no more… because it does. In amazing yields to boot.
I dunno if I would consider silver nitrate “green” really. I’m not aware that it causes flipperbabies, though I have no direct experience with feeding it to anything. Apparently fish don’t much care for it; indeed upon their writhing death I’m sure they rather hate it. So, this is an odd journal to stick this in.



Assemble combinatorial libraries. Search for pharmacophores. Tricyclics with nitrogens ought to do something geriatric Medicare-reimbursed. Go $Green.
All it lacks is stereoselectivity. Chiral silver helicate complexes are in the literature. If all else fails, how ’bout hydrogenation and new engineering nylon polymers?
Cool find. I wonder what oher metals would form the required eta-2 complex (Zn?). It would be fun to look at chiral auxiliaries to see if you induce stero-selectivity…
Are you suggesting that some of these yeilds may be exagurated?
It strikes me as odd. But I’m not calling him out on it. The mechanism doesn’t make me feel too good either, but… meh.
Some of these green reactions are really quite convenient. I have to agree with you about the Ag(I) though. It tends to disrupt ecosystems because it’s a good antibacterial agent. Is there another nice soft electrophile that could substitute? Probably Hg…
Wouldn’t that be worse? Or were you joking?
I don’t think AgNO3 is green either. Would these people consider di-methyl mercury as “green” too?