Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

被引：7

作者：

Wakayama, Fumika ^{[1
]}

Ito, Ryo ^{[1
]}

Park, Kwihwan ^{[1
]}

Ishida, Moeka ^{[1
]}

Yamada, Yutaro ^{[1
]}

Ichihara, Shuta ^{[1
]}

Takada, Hitoshi ^{[2
]}

Nakamura, Shinji ^{[2
]}

Kato, Ayumu ^{[2
]}

Yamada, Tsuyoshi ^{[1
]}

Sajiki, Hironao ^{[1
]}

Monguchi, Yasunari ^{[1
,3
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Organ Chem, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan

[2] Organo Corp, R&D Ctr, Minami Ku, 4-4-1 Nishionuma, Sagamihara, Kanagawa 2520332, Japan

[3] Daiichi Univ Pharm, Lab Organ Chem, Minami Ku, 22-1 Tatnagawa Machi, Fukuoka 8158511, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2021年 / 94卷 / 11期

关键词：

Amphipathic monolithic-resin; Continuous-flow reaction; Esterification; EFFICIENT ESTERIFICATION; SULFONIC-ACID; CATALYST; SOLVENT; GREEN;

D O I：

10.1246/bcsj.20210266

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.5-5.0 equiv) in toluene at 60-80 degrees C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 degrees C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

引用

页码：2702 / 2710

页数：9

共 53 条

[1] Material encapsulation in poly(methyl methacrylate) shell: A review [J].

Ahangaran, Fatemeh ;

Navarchian, Amir H. ;

Picchioni, Francesco .

JOURNAL OF APPLIED POLYMER SCIENCE, 2019, 136 (41)

[2] A Review of the Properties and Applications of Poly (Methyl Methacrylate) (PMMA) [J].

Ali, Umar ;

Abd Karim, Khairil Juhanni Bt. ;

Buang, Nor Aziah .

POLYMER REVIEWS, 2015, 55 (04) :678-705

[3] An uncommon use of irradiated flavins: Bronsted acid catalysis [J].

Arakawa, Yukihiro ;

Mihara, Tomohiro ;

Fujii, Hiroki ;

Minagawa, Keiji ;

Imada, Yasushi .

CHEMICAL COMMUNICATIONS, 2020, 56 (42) :5661-5664

[4] In-Water and Neat Batch and Continuous-Flow Direct Esterification and Transesterification by a Porous Polymeric Acid Catalyst [J].

Baek, Heeyoel ;

Minakawa, Maki ;

Yamada, Yoichi M. A. ;

Han, Jin Wook ;

Uozumi, Yasuhiro .

SCIENTIFIC REPORTS, 2016, 6

[5] Protic Acid Immobilized on Solid Support as an Extremely Efficient Recyclable Catalyst System for a Direct and Atom Economical Esterification of Carboxylic Acids with Alcohols [J].

Chakraborti, Asit K. ;

Singh, Bavneet ;

Chankeshwara, Sunay V. ;

Patel, Alpesh R. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :5967-5974

[6] The first insoluble polymer-bound palladium complexes of 2-pyridyldiphenylphosphine: highly efficient catalysts for the alkoxycarbonylation of terminal alkynes [J].

Doherty, S ;

Knight, JG ;

Betham, M .

CHEMICAL COMMUNICATIONS, 2006, (01) :88-90

[7] Synthesis of Sulfonic Acid Containing Ionic-Liquid-Based Periodic Mesoporous Organosilica and Study of Its Catalytic Performance in the Esterification of Carboxylic Acids [J].

Elhamifar, Dawood ;

Karimi, Babak ;

Moradi, Abbas ;

Rastegar, Javad .

CHEMPLUSCHEM, 2014, 79 (08) :1147-1152

[8] Reusable Heterogeneous Tungstophosphoric Acid-Derived Catalyst for Green Esterification of Carboxylic Acids [J].

Fiorio, Jhonatan Luiz ;

Braga, Adriano Henrique ;

Barbosa Guedes, Carmen Luisa ;

Rossi, Liane Marcia .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (19) :15874-15883

[9] Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation [J].

Funatomi, Takashi ;

Wakasugi, Kazunori ;

Misaki, Tomonori ;

Tanabe, Yoo .

GREEN CHEMISTRY, 2006, 8 (12) :1022-1027

[10] Tandem Acyl Substitution/Michael Addition of Thioesters with Vinylmagnesium Bromide [J].

Hirschbeck, Vera ;

Boeldl, Marlene ;

Gehrtz, Paul H. ;

Fleischer, Ivana .

ORGANIC LETTERS, 2019, 21 (08) :2578-2582

← 1 2 3 4 5 6 →