UYANIK, Muhammet

J-GLOBAL         Last updated: May 8, 2019 at 04:21
 
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Name
UYANIK, Muhammet
URL
https://www.ishihara-lab.net/english/staff-members/muhammet-uyanik/
Affiliation
Nagoya University
Section
Graduate School of Engineering Molecular and Macromolecular Chemistry 1
Job title
Assistant Professor
Degree
Doctor(Nagoya University)
Research funding number
20452188
ORCID ID
https://orcid.org/0000-0002-9751-1952

Academic & Professional Experience

 
Apr 2007
   
 
Assistant Professor, Biotechnology, Graduate Scool of Engineering, Nagoya University
 
Apr 2007
 - 
Mar 2017
Assistant Professor, Graduate School of Engineering Department of Applied Chemistry, Chemical Engineering and Biotechnology, Nagoya University
 
Apr 2017
 - 
Today
Assistant Professor, Graduate School of Engineering Molecular and Macromolecular Chemistry 1, Nagoya University
 

Education

 
Apr 2000
 - 
Mar 2004
Chemical and Biological Engineering, Faculty of Engineering, Nagoya University
 
Apr 2004
 - 
Mar 2006
Applied Chemistry, Chemical Engineering and Biotechnology, Graduate School, Division of Engineering, Nagoya University
 
Apr 2006
 - 
Mar 2007
Applied Chemistry, Chemical Engineering and Biotechnology, Graduate School, Division of Engineering, Nagoya University
 

Committee Memberships

 
Jan 2013
 - 
Dec 2016
Turkish Journal of Chemistry (The Scientific and Technological Research Council of Turkey)  Editorial Board
 
Sep 2015
 - 
Mar 2016
Anatolian Conference on Synthetic Organic Chemistry (ACSOC II)  Scientific Committee
 

Awards & Honors

 
Mar 2017
The Chemical Society of Japan Award for Young Chemists, Development of Selective Oxidation Reactions Using Designer Iodine Catalysts
Winner: Muhammet UYANIK
 
Jan 2016
Thieme Chemistry Journals Award, Thieme Publishing Group
 
Oct 2015
Banyu Chemist Award (BCA), Banyu Life Science Foundation International
 
Jul 2015
The 4th Green&Sustainable Chemistry (GSC) Encouragement Award, The Japan Association for Chemical Innovation (JACI)
 
Feb 2015
7th Inoue Science Research Award, Inoue Foundation for Science
 
Apr 2013
The Commendation for Science and Technology by the Minister of Education, Culture, Sports, Science and Technology, The Young Scientists' Prize, Ministry of Education, Culture, Sports, Science and Technology, Japan
 
Sep 2012
The 15th SIS Symposium Poster Award, The Society of Iodine Science (SIS)
 
Mar 2012
The Young Scholar Lectureship Award of the CSJ, The Chemical Society of Japan
 
Feb 2012
The Grand Prize of 6th Wakashachi Incentive Award, Aichi Prefectural Government
 
Mar 2011
Akazaki Prize, Nagoya University
 
May 2010
2010 Incentive Award for Young Scientist, Tokai Branch of The Society of Synthetic Organic Chemistry, The Society of Synthetic Organic Chemistry, Japan
 
Apr 2009
89th Annual Meeting of The Chemical Society of Japan, Best Presentation Award (Academic), The Chemical Society of Japan
 
Feb 2009
Shionogi Award in Synthetic Organic Chemistry (Japan), The Society of Synthetic Organic Chemistry, Japan
 
Apr 2008
88th Annual Meeting of The Chemical Society of Japan, Best Presentation Award (Academic), The Chemical Society of Japan
 
Mar 2008
The Green & Sustainable Chemistry Poster Award, Green & Sustainable Chemistry Network, Japan
 

Published Papers

 
Muhammet Uyanik, Kohei Nishioka, Kazuaki Ishihara
Chem. Lett.   48(4) 353-356   Mar 2019   [Refereed]
Muhammet Uyanik, Naoto Sahara, Kazuaki Ishihara
Eur. J. Org. Chem.   2019(1) 27-31   Jan 2019   [Refereed][Invited]
Takahiro Suzuki, Soichiro Watanabe, Muhammet Uyanik, Kazuaki Ishihara, Susumu Kobayashi, Keiji Tanino
Organic Letters   20(20) 3919-3922   Jul 2018   [Refereed]
The total synthesis of pestheic acid based on an intramolecular SNAr reaction without a nitro group and the asymmetric synthesis of (-)-maldoxin by a catalytic enantioselective oxidative dearomatization of pestheic acid are described. The reactiv...
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
J. Org. Chem.   82(22) 11946-11953   Nov 2017   [Refereed]
Highly enantioselective oxidative dearomatization of 2-naphthol derivatives was achieved for the first time by using conformationally flexible organoiodine catalysts derived from 2-aminoalcohol as a chiral source. Moreover, with the use of these ...
Muhammet Uyanik, Kohei Nishioka, Kazuaki Ishihara
Heterocycles   95(2) 1132-1147   Apr 2017   [Refereed][Invited]
Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and t...
Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara
Angew. Chem. Int. Ed.   56(14) 3956-3960   Mar 2017   [Refereed]
A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Furthermore, both the reaction rate and...
Muhammet Uyanik, Niiha Sasakura, Masahiro Mizuno, Kazuaki Ishihara
ACS Catal.   7(1) 872-876   Jan 2017   [Refereed]
A highly enantioselective oxidative dearomatization of ortho- and para-hydroquinone derivatives to the corresponding masked ortho- and para-benzoquinones has been achieved by using chiral organoiodine(III) catalysts.
Muhammet Uyanik, Kazuaki Ishihara
45(12) 16-24   Dec 2016   [Invited]
Muhammet Uyanik, Hiroki Hayashi, Hirokazu Iwata, Kazuaki Ishihara
Chem. Lett.   45(3) 353-355   Mar 2016   [Refereed]
2-Acyl tetrahydrofuran is a fundamental structure in natural products and pharmaceuticals. We achieved a chiral quaternary ammonium hypoiodite salt-catalyzed enantioselective oxidative cycloetherification of δ-hydroxyketone derivatives. The corr...
Muhammet Uyanik, Niiha Sasakura, Mitsuyoshi Kuwahata, Yasukazu Ejima, Kazuaki Ishihara
Chem. Lett.   44(3) 381-383   Mar 2015   [Refereed]
A highly efficient and practical oxidative dearomatization of phenols using sodium hypochlorite pentahydrate as an inexpensive, strong oxidant is reported for the first time. The oxidation reactions proceeded very rapidly in the presence of water ...
Muhammet Uyanik, Daisuke Suzuki, Mizu Watanabe, Hiroyasu Tanaka, Kikuo Furukawa, Kazuaki Ishihara
Chem. Lett.   44(3) 387-389   Mar 2015   [Refereed]
Highly efficient hypoiodite-catalyzed oxylactonization of aliphatic γ-oxocarboxylic acids to the corresponding γ-acyl-γ-butyrolactones was developed. Highly dilute reaction conditions and slow addition of the oxidant are each highly effective for ...
Muhammet Uyanik, Niiha Sasakura, Erina Kaneko, Kento Ohori, Kazuaki Ishihara
Chem. Lett.   44(2) 179-181   Feb 2015   [Refereed]
A highly enantioselective oxidative dearomatization of 1-naphthol derivatives (Kita spirolactonization) catalyzed by chiral hypoiodite species prepared in situ from chiral quaternary ammonium iodide in the presence of hydrogen peroxide is reported.
Muhammet Uyanik, Hiroki Hayashi, Kazuaki Ishihara
Science   345(6194) 291-294   Jul 2014   [Refereed]
The diverse biological activities of tocopherols and their analogs have inspired considerable interest in the development of routes for their efficient asymmetric synthesis. Here, we report that chiral ammonium hypoiodite salts catalyze highly che...
Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara
Wako Junyaku Jiho   81(4) 5-9   Oct 2013   [Invited]
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
Angew. Chem. Int. Ed.   52(35) 9215-9218   Aug 2013   [Refereed]
A conformationally flexible C2-symmetric organoiodine(III) catalyst for the highly enantioselective catalytic oxidative dearomatization of phenols has been developed. Catalysis is controlled by intramolecular hydrogen-bonding interactions and addi...
Muhammet Uyanik, Kazuaki Ishihara
ACS Catalysis   3(5) 513-520   Feb 2013   [Refereed][Invited]
The Baeyer-Villiger (BV) oxidation of carbonyl compounds to the corresponding esters or lactones is one of the most important transformations. We recently introduced a highly efficient and selective LiB(C6F5)4- or Ca[B(C6F5)4]2-catalyzed BV oxidat...
Muhammet Uyanik, Kazuaki Ishihara
J. Synth. Org, Chem., Jpn.   70(11) 1116-1122   Nov 2012   [Refereed][Invited]
The development of chiral hypervalent iodine-catalyzed oxidative transformations is one of the most challenging areas in asymmetric organocatalysis. Although several elegant chiral hypervalent iodine (III and V) reagents or catalysts had been dev...
Muhammet Uyanik, Daisuke Nakashima, Kazuaki Ishihara
Angew. Chem. Int. Ed.   51(36) 9093-9096   Sep 2012   [Refereed]
We have developed highly efficient and selective Li[B(C6F5)4] or Ca[B(C6F5)4]2 catalyzed Baeyer-Villiger (BV) oxidations of various cycloalkanones with 30-wt% aqueous hydrogen peroxide to give the corresponding lactones in high yield. Additionally...
Muhammet Uyanik
Chemistry and Chemical Industry   65(8) 625-626   Aug 2012   [Refereed]
Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara
Molecules   17(7) 8604-8616   Jul 2012   [Refereed][Invited]
We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to ortho-quinones. Various phenols could be oxidized to the corresponding ortho-quinones in good to excellent yields using catalytic amounts...
Muhammet Uyanik, Kazuaki Ishihara
ChemCatChem   4(2) 177-185   Feb 2012   [Refereed][Invited]
This Concept highlights the discovery and development of oxidative coupling reactions catalyzed by the hypoiodite (IO) or iodite (IO2) ion, which are generated in situ from iodide (I-) ion with hydrogen peroxide or tert-butyl hydroperoxide as an e...
Muhammet Uyanik, Kazuaki Ishihara, Margaret Faul, Richard Crockett
Org. Synth.   89 105-114   Sep 2011   [Refereed][Invited]
We have reported that 2-iodoxybenzenesulfonic acids (IBSs) which are in situ prepared from Oxone and 2-iodobenzenesulfonic acids show efficient catalytic activity on the alcohol oxidation under mild conditions. Here, we succeeded in scale up of th...
Muhammet Uyanik, Daisuke Suzuki, Takeshi Yasui, Kazuaki Ishihara
Angew. Chem. Int. Ed.   50(23) 5331-5334   May 2011   [Refereed]
The intra- and intermolecular title reaction is catalyzed by an in situ generated ammonium (hypo)iodite species. Either H2O2 or tert-butyl hydroperoxide (TBHP) can be used as an environmentally benign oxidant and a wide range of substrates react t...
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
Wako Junyaku Jiho   79(2) 2-5   Apr 2011   [Invited]
Muhammet Uyanik, Kazuaki Ishihara
Chimica Oggi-Chemistry Today   29(1) 18-21   Jan 2011   [Refereed][Invited]
Very recently, we developed the first enantioselective oxidative cycloetherification of ketophenols to 2-acyl-2,3-dihydrobenzofuran derivatives catalysed by in situ generated chiral quaternary ammonium (hypo)iodite with hydrogen peroxide or tert-b...
Muhammet Uyanik, Kazuaki Ishihara
Aldrichim. Acta   43(3) 83-91   Dec 2010   [Refereed][Invited]
The oxidation of alcohols to the corresponding carbonyl compounds is one of the most important transformations in synthetic organic chemistry. Over the past two decades, hypervalent iodine compounds have received a great deal of attention due to t...
Kazuaki Ishihara, Muhammet Uyanik
Kagaku   65(10) 12-17   Sep 2010   [Invited]
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
Tetrahedron   66(31) 5841-5851   Jul 2010   [Refereed][Invited]
We demonstrate here the rational design of a conformationally flexible C2-symmetric iodosylarene 8g based on secondary n-sigma* or hydrogen-bonding interactions as a chiral catalyst for the enantioselective Kita oxidative spirolactonization of 1-n...
Muhammet Uyanik, Hiroaki Okamoto, Takeshi Yasui, Kazuaki Ishihara
Science   328(5984) 1376-1379   Jun 2010   [Refereed]
It is desirable to minimize the use of rare or toxic metals for oxidative reactions in the synthesis of pharmaceutical products. Hypervalent iodine compounds are environmentally benign alternatives, but their catalytic use, particularly for asymme...
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
Angew. Chem. Int. Ed.   49(12) 2175-2177   Mar 2010   [Refereed]
Conformationally flexible C2-symmetric chiral iodosylarene, which has been rationally designed based on secondary n-σ* or hydrogen-bonding interactions, is a highly effective catalyst for the Kita oxidative spirolactonization. The present catalys...
Muhammet Uyanik, Ryota Fukatsu, Kazuaki Ishihara
Chem. Asian J.   5(3) 456-460   Mar 2010   [Refereed][Invited]
We demonstrated that a simple and environmentally benign catalytic system HBr/NaNO2 is very effective for the selective oxidation of alcohols under balloon pressure of O2. Furthermore, the aerobic oxidation of alcohols was also achieved under ball...
Muhammet Uyanik, Ryota Fukatsu, Kazuaki Ishihara
Org. Lett.   11(15) 3470-3473   Aug 2009   [Refereed]
A 2-iodoxybenzenesulfonic acid (IBS)-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with powdered Oxone in the presence of potassium carbonate and tetrabutylammonium hydrogen sulfate has been developed.
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
Bioorg. Med. Chem. Lett.   19(14) 3848-3851   Jul 2009   [Refereed][Invited]
The hypervalent iodine-catalyzed oxylactonization of ketocarboxylic acids to ketolactones was achieved in the presence of iodobenzene (10 mol%), p-toluenesulfonic acid monohydrate (20 mol%) and meta-chloroperbenzoic acid as a stoichiometric co-oxi...
Muhammet Uyanik, Kazuaki Ishihara
Chem. Commun.   2009(16) 2086-2099   Apr 2009   [Refereed][Invited]
Over the past two decades there has been a dramatic increse in the use of hypervalent iodine compounds in synthetic organic chemistry due to their mild and selective oxidizing properties. Hypervalent iodine compounds catalyze various oxidation rea...
Muhammet Uyanik, Matsujiro Akakura, Kazuaki Ishihara
J. Am. Chem. Soc.   131(1) 251-262   Jan 2009   [Refereed]
Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) were superior to IBX as catalysts for the oxidation of alcohols with Oxone under nonaqueous conditions. Furthermore, 2-iodoxybenzenesulfonic acid (IBS) was much more active than modi...
Muhammet Uyanik, Kazuaki Ishihara, Hisashi Yamamoto
Org. Lett.   8(24) 5649-5652   Nov 2006   [Refereed]
Highly diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4...
Muhammet Uyanik, Kazuaki Ishihara, Hisashi Yamamoto
Bioorg. Med. Chem.   13(17) 5055-5065   Sep 2005   [Refereed][Invited]
Asymmetric total syntheses of acid-sensitive (-)- and (+)-caparrapi oxides (1) and (+)-8-epicaparrapi oxide (2) from farnesol (10) are achieved using Sharpless-Katsuki epoxidation and Lewis acid-assisted chiral Br?nsted acid (chiral LBA)-induced p...
Muhammet Uyanik, Hideaki Ishibashi, Kazuaki Ishihara, Hisashi Yamamoto
Org. Lett.   7(8) 1601-1604   Apr 2005   [Refereed]
Asymmetric total syntheses of acid-sensitive (-)-caparrapi oxide (1) and (+)-8-epicaparrapi oxide (2) from farnesol (9) were achieved using Sharpless-Katsuki epoxidation and Lewis acid-assisted chiral Brnsted acid (chiral LBA)-induced polyene cycl...

Misc

 
Muhammet Uyanik, Naoto Sahara, Kazuaki Ishihara
Eur. J. Org. Chem.   in press   Oct 2018   [Refereed]
Takahiro Suzuki, Soichiro Watanabe, Muhammet Uyanik, Kazuaki Ishihara, Susumu Kobayashi, Keiji Tanino
Organic Letters   20(20) 3919-3922   Jul 2018   [Refereed]
The total synthesis of pestheic acid based on an intramolecular SNAr reaction without a nitro group and the asymmetric synthesis of (-)-maldoxin by a catalytic enantioselective oxidative dearomatization of pestheic acid are described. The reactiv...
Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara
J. Org. Chem.   82(22) 11946-11953   Nov 2017   [Refereed]
Highly enantioselective oxidative dearomatization of 2-naphthol derivatives was achieved for the first time by using conformationally flexible organoiodine catalysts derived from 2-aminoalcohol as a chiral source. Moreover, with the use of these ...
Muhammet Uyanik, Kohei Nishioka, Kazuaki Ishihara
Heterocycles   95(2) 1132-1147   Apr 2017   [Refereed][Invited]
Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and t...
Muhammet Uyanik, Tatsuya Mutsuga, Kazuaki Ishihara
Angew. Chem. Int. Ed.   56(14) 3956-3960   Mar 2017   [Refereed]
A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Furthermore, both the reaction rate and...

Books etc

 
Muhammet Uyanik, Kazuaki Ishihara (Part:Joint Work)
John Wiley & Sons: Chichester   Sep 2018   
Muhammet Uyanik, Kazuaki Ishihara (Part:Joint Work)
Georg Thieme-Verlag KG   Oct 2017   ISBN:978-3-13-201231-8
Muhammet Uyanik, Kazuaki Ishihara (Part:Joint Work)
John Wiley & Sons: Weinheim   Jun 2016   ISBN:978-3-527-33851-1
K. C. Nicolaou, Tamsyn Montagnon, Phil S. Baran, Muhammet Uyanik, Kazuaki Ishihara (Part:Joint Work)
John Wiley & Sons, Ltd   Sep 2012   ISBN:9780470842898

Conference Activities & Talks

 
IBS-catalyzed Highly Efficient and Selective Oxidation and Oxidative Esterification of Alcohols with Oxone
Ryutaro Kondo, Muhammet Uyanik, Kazuaki Ishihara
The 99th Annual Meeting of CSJ   16 Mar 2019   
Hypoiodite-catalyzed Chemoselective Generation of Quinone Methides and Application to Tandem Reactions
Kohei Nishioka, Muhammet Uyanik, Kazuaki Ishihara
The 99th Annual Meeting of CSJ   16 Mar 2019   
High-Performance Hypohalite Catalysis for Enantioselective Oxidative Dearomatization of Phenols
Takehiro Kato, Naoto Sahara, Muhammet Uyanik, Kazuaki Ishihara
The 99th Annual Meeting of CSJ   16 Mar 2019   
Chiral Quaternary Ammonium Salt-catalyzed Enantioselective Oxidative Dearomatizative Chlorination of Naphthols
Outa Katade, Naoto Sahara, Muhammet Uyanik, Kazuaki Ishihara
The 99th Annual Meeting of CSJ   16 Mar 2019   
Chiral Hypoiodite-catalyzed Enantioselective Oxidative α-Azidation of Carbonyl Compounds
Naoto Sahara, Muhammet Uyanik, Kazuaki Ishihara
The 99th Annual Meeting of CSJ   16 Mar 2019   

Works

 
Development of Novel Oxidation Catalyst Systems Using Designer Iodine Catalysis
The Others   Jan 2016
High-Turnover Hypoiodite Catalysis for Enantioselective Synthesis of Chromans
The Others   Jul 2014
Enantioselective Oxidative Transformations Using Designer Iodine Catalysis
The Others   Nov 2011

Research Grants & Projects

 
Development of Selective Oxidation Reactions Using Iodine Catalysis
Japan Society for the Promotion of Science: Grants-in-Aid for Scientific Research
Project Year: Apr 2018 - Mar 2021
Development of Oxidative Coupling Reactions Using Designer Iodine Catalysts
Japan Society for the Promotion of Science: Grants-in-Aid for Scientific Research
Project Year: Apr 2015 - Mar 2018
High-Turnover Hypoiodite Catalysis of Enantioselective Oxidative Cycloetherification to Synthesize Optically Active Tocopherols
Project Year: Jul 2014   
Oxidative C-C Coupling Reactions Using Organocatalysis
Japan Society for the Promotion of Science: Grants-in-Aid for Scientific Research
Project Year: Apr 2013 - Mar 2014
Development of Onium (Hypo)iodite Salt-Catalyzed Oxidative Coupling Reactions Using Hydrogen Peroxide or Molecular Oxygen
Ministry of Education, Culture, Sports, Science and Technology: Grants-in-Aid for Scientific Research
Project Year: Apr 2013 - Mar 2015

Patents

 
特開2016-74614 : New alkyl carbonyl lactone compounds and method for producing thereof
Kazuaki Ishihara, Muhammet Uyanik, Kikuo Furukawa, Hiroyasu Tanaka
特開2015-168660 : Method for producing aryl hydroquinone derivative and aryl quinone derivative
Kazuaki Ishihara, Muhammet Uyanik
特許第6115946号 : Method for producing optically active aromatic compounds having ring structure that includes nitrogen atom
Kazuaki Ishihara, Muhammet Uyanik, Daisuke Suzuki
JP/WO2013/121879(A1) : Production method for nitrogen-containing cyclic compound, and nitrogen-containing cyclic compound
Kazuaki Ishihara, Muhammet Uyanik
JP/WO2013/121873(A1) : Production method for biaryl compound
Kazuaki Ishihara, Muhammet Uyanik