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Alkali-Metal-Catalyzed Addition of Phosphines to Carbodiimides:
A General and Efficient Route to Phosphaguanidines
Wen-Xiong Zhang, Masayoshi Nishiura and Zhaomin Hou*
Organometallic Chemistry Laboratory, RIKEN, Hirosawa 2-1, Wako, Saitama 351-0198, Japan
[email protected]
Catalytic addition of phosphine R2PH bonds across the CN double bond of carbodiimides
(RN=C=NR) could be, in principle, a straightforward and atom-economical route to
substituted
phosphaguanidines
RN=C(PR2)(NHR),
an
important
class
of
heteroatom-containing compounds which may be used as building blocks for organic
synthesis and as unique ligands for various metal complexes. However, such catalytic process
has been hardly explored. We report here a novel catalytic synthesis of phosphaguanidines by
alkali-metal-catalyzed addition of various phosphines to carbodiimides as shown in eq. 1.[1]
R
R2
P H
R3
+
R N C N R1
(Me3Si)2NK (1 mol%)
R2
N
(1)
P
THF, r.t.
R3
N
H
R1
[1] W. -X. Zhang, M. Nishiura and Z. Hou, Chem. Commun. 3812 (2006).
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