Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent

David M Heard; Alastair J J Lennox

doi:10.1021/acs.orglett.1c00850

Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent

David M Heard, Alastair J J Lennox^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Letter (Academic Journal) › peer-review

8 Citations (Scopus)

143 Downloads (Pure)

Abstract

Dichloromeldrum’s acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

Original language	English
Pages (from-to)	3368-3372
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	9
Early online date	12 Apr 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00850
Publication status	Published - 7 May 2021

Bibliographical note

Funding Information:
We would like to thank the Royal Society (University Research Fellowship and Enhancement award to A.J.J.L.) and EPSRC (EP/T001631/1) for funding.

Publisher Copyright:
© 2021 American Chemical Society.

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title = "Dichloromeldrum{\textquoteright}s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent",

abstract = "Dichloromeldrum{\textquoteright}s acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.",

author = "Heard, {David M} and Lennox, {Alastair J J}",

note = "Funding Information: We would like to thank the Royal Society (University Research Fellowship and Enhancement award to A.J.J.L.) and EPSRC (EP/T001631/1) for funding. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c00850",

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T1 - Dichloromeldrum’s Acid (DiCMA)

T2 - A Practical and Green Amine Dichloroacetylation Reagent

AU - Heard, David M

AU - Lennox, Alastair J J

N1 - Funding Information: We would like to thank the Royal Society (University Research Fellowship and Enhancement award to A.J.J.L.) and EPSRC (EP/T001631/1) for funding. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/5/7

Y1 - 2021/5/7

N2 - Dichloromeldrum’s acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

AB - Dichloromeldrum’s acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

U2 - 10.1021/acs.orglett.1c00850

DO - 10.1021/acs.orglett.1c00850

M3 - Letter (Academic Journal)

C2 - 33844547

SN - 1523-7060

VL - 23

SP - 3368

EP - 3372

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent

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