An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide.
It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives.
Xu
Xiaoliang
X
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China.
Li
Xiaonian
X
Ma
Lei
L
Ye
Ning
N
Weng
Bojie
B
D000578:Amidines / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D013237:Stereoisomerism
D000578:Amidines; D000588:Amines; D001386:Azides; D001391:Azo Compounds