Categories: C-N Bond Formation > Amines >
Synthesis of 1,2-diamines
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Recent Literature
Indium tribromide catalyzes efficiently the aminolysis of activated
aziridines with aromatic amines under mild reaction conditions to afford the
corresponding vicinal-diamines in high yields with high selectivity.
J. S. Yadav, B. V. S. Reddy, K. Vishweshwar Rao, K. Saritha Raj, A. R.
Prasad, Synthesis,
2002, 1061-1064.
The aminolysis of meso-N-phenyl aziridines is efficiently
catalyzed by 1 mol% of Sc(OTf)3 and furnishes valuable 1,2-diamines
in good to excellent yields.
S. Peruncheralathan, M. Henze, C. Schneider, Synlett, 2007,
2289-2291.
The use of CuCl as catalyst and di-tert-butylthiadiaziridine 1,1-dioxide
as nitrogen source allows an effective diamination of activated terminal olefins
in good yields under mild reaction conditions.
B. Zhao, W. Yuan, H. Du, Y. Shi, Org. Lett., 2007,
9, 4943-4945.
The use of di-t-butyldiaziridinone as
nitrogen source and a N-heterocyclic carbene-Pd(0) complex as catalyst
allows an efficient diamination of a wide
variety of conjugated dienes and trienes in good
yields with high regio- and stereoselectivities.
L. Xu, H. Du, Y. Shi, J. Org. Chem.,
2007,
72, 7038-7041.
A wide variety of terminal olefins can be effectively diaminated at allylic and
homoallylic carbons via formal C-H activation in good yields with high
stereoselectivity using di-tert-butyldiaziridinone as nitrogen source and
Pd(PPh3)4 as catalyst.
H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc., 2007,
129, 7496-7497.
A remarkable Pd-catalyzed diamination of unactivated alkenes using N-fluorobenzenesulfonimide
(NFBS) as an aminating reagent is described. The reaction incorporates one
nitrogen donor from the substrate and the other from the NFBS, thereby
generating cyclic diamine derivatives in a single step. The products are
differentially protected at both nitrogens, allowing for maximal synthetic
flexibility.
P. A. Sibbald, F. E. Michael, Org. Lett., 2009,
11, 1147-1149.
A palladium-catalyzed intramolecular diamination reaction yields cyclic
ureas as direct products of an oxidative alkene transformation in the
presence of iodosobenzene diacetate as terminal oxidant.
J. Streuff, C. H. Hövelmann, M. Nieger, K. Muniz, J. Am. Chem. Soc.,
2005,
127, 14586-14587.
