Lewis Acid Assisted Brønsted Acid Catalysed Decarbonylation of Isocyanates

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Dasgupta, Ayan
van Ingen, Yara
Guerzoni, Michael G.
Farshadfar, Kaveh
Rawson, Jeremy M.
Richards, Emma
Ariafard, Alireza
Melen, Rebecca L.

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Abstract

An efficient and mild reaction protocol for the decarbonylation of isocyanates has been developed using catalytic amounts of Lewis acidic boranes. The electronic nature (electron withdrawing, electron neutral, and electron donating) and the position of the substituents (ortho/meta/para) bound to isocyanate controls the chain length and composition of the products formed in the reaction. Detailed DFT studies were undertaken to account for the formation of the mono/di-carboxamidation products and benzoxazolone compounds.

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Chemistry - A European Journal

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