KFU. Card publication. Amphiphilic Pd (II)-NHC complexes on 1,3-alternate p-tertbutylthiacalix[4]arene platform: synthesis and catalytic activities in coupling and hydrogenation reactions

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AMPHIPHILIC PD (II)-NHC COMPLEXES ON 1,3-ALTERNATE P-TERTBUTYLTHIACALIX[4]ARENE PLATFORM: SYNTHESIS AND CATALYTIC ACTIVITIES IN COUPLING AND HYDROGENATION REACTIONS

Form of presentation

Articles in international journals and collections

Year of publication

2020

Authors, employees of KFU

Antipin Igor Sergeevich, author

Burilov Vladimir Aleksandrovich, author

Evtyugin Vladimir Gennadevich, author

Islamov Daut Rinatovich, author

Mironova Diana Aleksandrovna, author

Osin Yuriy Nikolaevich, author

Soloveva Svetlana Evgenevna, author

Sultanova Elza Damirovna, author

Usachev Konstantin Sergeevich, author

Authors, postgraduates KFU

Gafiatullin Bulat Khalimovich, postgraduate kfu

Bibliographic description in the original language

V.A. Burilov, B.H.Gafiatullin, D.A. Mironova, E.D. Sultanova, V. Evtugyn, Y. Osin, D. Islamov, K. Usachev, S. Solovieva I. Antipin, Amphiphilic Pd (II)-NHC complexes on 1,3-alternate p-tertbutylthiacalix[4]arene platform: synthesis and catalytic activities in coupling and hydrogenation reactions. European Journal of Organic Chemistry., 2020 (2020), 2153

Annotation

Herein we report the first example of amphiphilic PdII?NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII?NHC complexes in Suzuki?Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki?Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2‐fold increase of conversion of 4‐bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. PdII?NHC complexes demonstrated a high activity in model hydrogenation reaction of p‐nitrophenol using sodium borohydride. The most lipophilic PdII?NHC complex was found to be most active, which can be attributed with additional p‐nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle.

Keywords

NHC complex, thiacalix[4]arene, suzuki coupling, micellar catalysis, catalytic hydrogenation

URL

https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202000059

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=249805&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Antipin Igor Sergeevich	ru_RU
dc.contributor.author	Burilov Vladimir Aleksandrovich	ru_RU
dc.contributor.author	Evtyugin Vladimir Gennadevich	ru_RU
dc.contributor.author	Islamov Daut Rinatovich	ru_RU
dc.contributor.author	Mironova Diana Aleksandrovna	ru_RU
dc.contributor.author	Osin Yuriy Nikolaevich	ru_RU
dc.contributor.author	Soloveva Svetlana Evgenevna	ru_RU
dc.contributor.author	Sultanova Elza Damirovna	ru_RU
dc.contributor.author	Usachev Konstantin Sergeevich	ru_RU
dc.contributor.author	Gafiatullin Bulat Khalimovich	ru_RU
dc.date.accessioned	2020-01-01T00:00:00Z	ru_RU
dc.date.available	2020-01-01T00:00:00Z	ru_RU
dc.date.issued	2020	ru_RU
dc.identifier.citation	V.A. Burilov, B.H.Gafiatullin, D.A. Mironova, E.D. Sultanova, V. Evtugyn, Y. Osin, D. Islamov, K. Usachev, S. Solovieva I. Antipin, Amphiphilic Pd (II)-NHC complexes on 1,3-alternate p-tertbutylthiacalix[4]arene platform: synthesis and catalytic activities in coupling and hydrogenation reactions. European Journal of Organic Chemistry., 2020 (2020), 2153	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=249805&p_lang=2	ru_RU
dc.description.abstract	Herein we report the first example of amphiphilic PdII?NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII?NHC complexes in Suzuki?Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki?Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2‐fold increase of conversion of 4‐bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. PdII?NHC complexes demonstrated a high activity in model hydrogenation reaction of p‐nitrophenol using sodium borohydride. The most lipophilic PdII?NHC complex was found to be most active, which can be attributed with additional p‐nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	NHC complex	ru_RU
dc.subject	thiacalix[4]arene	ru_RU
dc.subject	suzuki coupling	ru_RU
dc.subject	micellar catalysis	ru_RU
dc.subject	catalytic hydrogenation	ru_RU
dc.title	Amphiphilic Pd (II)-NHC complexes on 1,3-alternate p-tertbutylthiacalix[4]arene platform: synthesis and catalytic activities in coupling and hydrogenation reactions	ru_RU
dc.type	Articles in international journals and collections	ru_RU