Lewis Acid Assisted Brønsted Acid Catalysed Decarbonylation of Isocyanates: A Combined DFT and Experimental Study

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

doi:10.1002/chem.202201422

Lewis Acid Assisted Brønsted Acid Catalysed Decarbonylation of Isocyanates: A Combined DFT and Experimental Study

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Article number	e202201422
Number of pages	7
Journal	Chemistry - A European Journal
Volume	28
Issue number	45
Early online date	13 May 2022
DOIs	https://doi.org/10.1002/chem.202201422
Publication status	Published - Aug 2022
Externally published	Yes

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10.1002/chem.202201422Licence: CC BY

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title = "Lewis Acid Assisted Br{\o}nsted Acid Catalysed Decarbonylation of Isocyanates: A Combined DFT and Experimental Study",

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.",

keywords = "biuret, boranes, DFT, isocyanate, urea",

author = "Ayan Dasgupta and \{van Ingen\}, Yara and Guerzoni, \{Michael G.\} and Kaveh Farshadfar and Rawson, \{Jeremy M.\} and Emma Richards and Alireza Ariafard and Melen, \{Rebecca L.\}",

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year = "2022",

month = aug,

doi = "10.1002/chem.202201422",

language = "English",

volume = "28",

journal = "Chemistry - A European Journal",

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T1 - Lewis Acid Assisted Brønsted Acid Catalysed Decarbonylation of Isocyanates

T2 - A Combined DFT and Experimental Study

AU - Dasgupta, Ayan

AU - van Ingen, Yara

AU - Guerzoni, Michael G.

AU - Farshadfar, Kaveh

AU - Rawson, Jeremy M.

AU - Richards, Emma

AU - Ariafard, Alireza

AU - Melen, Rebecca L.

PY - 2022/8

Y1 - 2022/8

N2 - 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.

AB - 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.

KW - biuret

KW - boranes

KW - DFT

KW - isocyanate

KW - urea

UR - https://www.scopus.com/pages/publications/85132139290

U2 - 10.1002/chem.202201422

DO - 10.1002/chem.202201422

M3 - Article

C2 - 35560742

AN - SCOPUS:85132139290

SN - 0947-6539

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 45

M1 - e202201422

ER -

Lewis Acid Assisted Brønsted Acid Catalysed Decarbonylation of Isocyanates: A Combined DFT and Experimental Study

Abstract

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