bleh, slipped into inactivity again. I blame Chara
🔴 we've been busy!
I know, I know, I'm kidding! anyway, let's do an _Organic Syntheses_ roulette again
the word is "compare"
oh haha I recognize the _first_ hit already, it came up once (think I might have posted that one to Twitter not here, it was a synthesis of an iridium(III) complex of 2-phenylpyridine
so here's the second hit
http://orgsyn.org/demo.aspx?prep=v95p0015
synthesis of a 2-substitute indole
slightly elaborate method, although conceptually it's simple enough: the precursors for the indole are N-acetylphenylhydroxyamine and a terminal alkyne, 1-hexyne, yielding N-acetyl-2-n-butylindole. the hitch is what's used for catalysis: zinc trifluoromethanesulfonate, the silver salt of N,N-bis(trifluoromethanesulfonyl)imine (a strong acid that supplies a _highly_ non-nucleophilic anion), and a complex of gold(I) with a very bulky triarylphosphite ligand, that needs to be made from scratch
well, that's neat I guess. can't imagine ever carrying this one out
looks like some _internal_ alkynes were used, yielding 2,3-disubstituted indoles with good regioselectivity (i.e. even though two possible indoles could be obtained, generally only one was obtained in quantity). it's not clear to me from the provided examples what controls the regioselectivity