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Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters. / Dar'In, Dmitry; Kantin, Grigory; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 51, No. 22, 01.01.2019, p. 4284-4290.

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@article{f97f7b9580564d8e9cff7de3dc692294,
title = "Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters",
abstract = "The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a separate activation step. Formylation in situ, followed by the addition of an optimized amount of the 'SAFE cocktail' (obtained by mixing sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water) led to the formation of the desired diazo compounds, which were isolated by extraction in moderate to excellent yields, and, in most cases, with no need for additional purification.",
keywords = "C-H acidity, deformylation, diazo transfer, formylation, water solubility, DIAZOKETONES, CLEAVAGE",
author = "Dmitry Dar'In and Grigory Kantin and Mikhail Krasavin",
year = "2019",
month = jan,
day = "1",
doi = "10.1055/s-0039-1690613",
language = "English",
volume = "51",
pages = "4284--4290",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "22",

}

RIS

TY - JOUR

T1 - Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a separate activation step. Formylation in situ, followed by the addition of an optimized amount of the 'SAFE cocktail' (obtained by mixing sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water) led to the formation of the desired diazo compounds, which were isolated by extraction in moderate to excellent yields, and, in most cases, with no need for additional purification.

AB - The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a separate activation step. Formylation in situ, followed by the addition of an optimized amount of the 'SAFE cocktail' (obtained by mixing sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water) led to the formation of the desired diazo compounds, which were isolated by extraction in moderate to excellent yields, and, in most cases, with no need for additional purification.

KW - C-H acidity

KW - deformylation

KW - diazo transfer

KW - formylation

KW - water solubility

KW - DIAZOKETONES

KW - CLEAVAGE

UR - http://www.scopus.com/inward/record.url?scp=85074229848&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690613

DO - 10.1055/s-0039-1690613

M3 - Article

AN - SCOPUS:85074229848

VL - 51

SP - 4284

EP - 4290

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 22

ER -

ID: 49033622