Categories: C=N Bond Formation >
Synthesis of carbodiimides
Recent Literature
An I2/CHP-mediated cross-coupling reaction of isocyanides with
readily accessible amines gives carbodiimides in good yields. This metal-free
strategy for coupling of isocyanides with amines provides an efficient approach
for symmetric and unsymmetric functionalized carbodiimide derivative synthesis
under mild conditions.
T.-H. Zhu, S.-Y. Wang, Y.-Q. Tao, S.-J. Ji, Org. Lett.,
2015,
17, 1974-1977.
An efficient and mild oxidative desulfurization procedure using o-iodoxybenzoic
acid enables the synthesis of carbodiimides starting from easily available
1,3-disubstituted thioureas.
P. S. Chaudhari, P. S. Dangate, K. G. Akamanchi, Synlett, 2010,
3065-3067.
Dehydrosulfurization using a hypervalent iodine(III) reagent enables a simple
and efficient preparation of symmetrical and unsymmetrical carbodiimides from
the corresponding thioureas. The oxidation afforded carbodiimides in excellent
yields and high selectivity. A possible mechanism for the transformation is
proposed.
C. Zhu, D. Xu, Y. Wei, Synthesis, 2011,
711-714.
An electrochemical oxidative cross-coupling of amines with aryl and aliphatic
isocyanides proceeds without involving any transition-metal catalyst, oxidant,
or toxic reagents in an undivided cell to provide carbodiimides in good yields
with H2 as the only byproduct. A subsequent optional hydrolysis
provides ureas in situ.
B. K. Malviya, P. K. Jaiswal, V. P. Verma, S. S. Badsara, S. Sharma,
Org. Lett., 2020, 22, 2323-2327.
Sequential Pd(0)/Fe(III) catalysis enables a rapid and efficient synthesis of
aminotetrazoles from aryl azides, isocyanides, and TMSN3. The reaction
sequence utilizes a Pd-catalyzed azide-isocyanide denitrogenative coupling
to generate an unsymmetric carbodiimide, which reacts with TMSN3
in the presence of FeCl3 in a single pot.
R. S. Pathare, A. J. Ansari, S. Verma, A. Maurya, A. K. Maurya, V. K. Agnihotri,
A. Sharon, R. T. Pardasani, D. M. Sawant, J. Org. Chem., 2018, 83,
9530-9537.