Catalytic addition of alkyne C-H, amine N-H, and phosphine P-H bonds to carbodiimides: an efficient route to propiolamidines, guanidines, and phosphaguanidines.
Various metal complexes (e.g., lanthanides, early transition metals, and alkali metals) can serve as catalyst precursors for the catalytic addition of alkyne C-H, amine N-H, and phosphine P-H bonds to carbodiimides, to give a new family of propiolamidines, guanidines, and phosphaguanidines, some of which were difficult to prepare previously. The catalytic reaction proceeds generally through nucleophilic addition of an M-ER (E=CR(1)R(2), NR(1), PR(1)) bond, which is formed by an acid-base reaction between a catalyst precursor and a RE-H bond, to a carbodiimide compound, followed by protonolysis of the resultant amidinate-(phospha)guanidinate species "{R'NC(ER)NR'}M" with RE-H.
Zhang
Wen-Xiong
WX
Organometallic Chemistry Laboratory, RIKEN (The Institute of Physical and Chemical Research), Hirosawa 2-1, Wako, Saitama 351-0198, Japan. wx_zhang@pku.edu.cn
Hou
Zhaomin
Z
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D002384:Catalysis; D006146:Guanidines / Q000737:chemistry*; D007094:Imides / Q000737:chemistry; D015394:Molecular Structure; D017553:Phosphorus Compounds / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*
D000480:Alkynes; D000588:Amines; D002234:Carbodiimides; D006146:Guanidines; D007094:Imides; D017553:Phosphorus Compounds; D011422:Propionates; C011537:propiolic acid