Kabachnik-Fields and Prins-Ritter Synthesis: Application of
Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in
Comparative Study

J 2015

Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

HAVRÁNKOVÁ, Eva a Pavel PAZDERA

Základní údaje

Originální název

Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

Autoři

HAVRÁNKOVÁ, Eva a Pavel PAZDERA

Vydání

J Chem Applications, 2015, 2327-204X

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/15:00081736

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

alpha-Aminophosphonates; 4-Amidotetrahydropyranes; Metal catalysis; Polymer supported Ce(III); Solid support catalysis

Štítky

AKR, rivok

Změněno: 24. 5. 2016 10:03, doc. RNDr. Pavel Pazdera, CSc.

Anotace

V originále

We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of alpha-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of alpha-aminophosphonates, and 4-amidotetrahydropyrane derivatives.

Návaznosti

2A-1TP1/090, projekt VaV

Název: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministerstvo průmyslu a obchodu ČR, Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy

Citovat

HAVRÁNKOVÁ, Eva a Pavel PAZDERA. Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study. J Chem Applications. 2015, roč. 2, č. 1, s. 1-6. ISSN 2327-204X.

@article{1301126,
   author = {Havránková, Eva and Pazdera, Pavel},
   article_number = {1},
   keywords = {alpha-Aminophosphonates; 4-Amidotetrahydropyranes; Metal catalysis; Polymer supported Ce(III); Solid support catalysis},
   language = {eng},
   issn = {2327-204X},
   journal = {J Chem Applications},
   title = {Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study},
   url = {http://www.avensonline.org/wp-content/uploads/JCAP-02-2380-5021-0004.pdf},
   volume = {2},
   year = {2015}
}

TY  - JOUR
ID  - 1301126
AU  - Havránková, Eva - Pazdera, Pavel
PY  - 2015
TI  - Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study
JF  - J Chem Applications
VL  - 2
IS  - 1
SP  - 1-6
EP  - 1-6
SN  - 2327204X
KW  - alpha-Aminophosphonates
KW  - 4-Amidotetrahydropyranes
KW  - Metal catalysis
KW  - Polymer supported Ce(III)
KW  - Solid support catalysis
UR  - http://www.avensonline.org/wp-content/uploads/JCAP-02-2380-5021-0004.pdf
L2  - http://www.avensonline.org/wp-content/uploads/JCAP-02-2380-5021-0004.pdf
N2  - We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of alpha-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of alpha-aminophosphonates, and 4-amidotetrahydropyrane derivatives.
ER  -

HAVRÁNKOVÁ, Eva a Pavel PAZDERA. Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study. \textit{J Chem Applications}. 2015, roč.~2, č.~1, s.~1-6. ISSN~2327-204X.

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