Zinc Catalyzed Hydroamination of Carbodiimides/Isocyanate Leading to Guanidines/Urea Derivatives Formation and Lanthanides Mediated Oxidative Cross Coupling of Benzyl Alcohols and Various Amines to form corresponding Imines

Sachdeva, Mitali and Panda, Tarun K (2016) Zinc Catalyzed Hydroamination of Carbodiimides/Isocyanate Leading to Guanidines/Urea Derivatives Formation and Lanthanides Mediated Oxidative Cross Coupling of Benzyl Alcohols and Various Amines to form corresponding Imines. Masters thesis, Indian Institute of Technology Hyderabad.

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Abstract

In the chapter 1, we report the highly chemo-selective catalytic addition of N–H bonds from various aromatic amines to carbodiimides and isocyanates using (Ar-BIAO)ZnCl2 complexes [Ar-BIAO = N-(aryl)imino-acenapthenone, Ar = 2,6-Me2C6H3(1), 2,4,6 Me3C6H2(2), 2,6- iPr2C6H3(3)]as the pre-catalyst to prepare guanidines and urea derivatives in 55-90% yield. The complex 3 showed higher catalytic activity than analogous complexes 1 and 2under similar reaction conditions. The catalytic addition of N–H bonds into heterocumulenes displays a broad substrate scope. The amines having electron donating groups underwent higher conversion than the amines having electron withdrawing groups to afford corresponding guanidine or urea derivative. A possible mechanism involving penta-coordinated zinc transition state for the catalytic reaction is presented.

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