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