Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent “Click-Declick” Chemistry

Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent “Click-Declick” Chemistry Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2018, Том: 83, Номер: 17, Страницы: 9756-9773 Страниц : 18 DOI: 10.1021/acs.joc.8b01296

Авторы

Golovanov Ivan S. ¹ , Mazeina Galina S. ^1,2 , Nelyubina Yulia V. ³ , Novikov Roman A. ¹ , Mazur Anton S. ⁴ , Britvin Sergey N. ⁵ , Tartakovsky Vladimir A. ¹ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow 119991, Russia
2	Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, Moscow 125047, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilov Str. 28, Moscow 119991, Russia
4	Center for Magnetic Resonance, St. Petersburg State University, University Av. 26, St. Petersburg 198504, Russia
5	Department of Crystallography, St. Petersburg State University, Universitetskaya Nab. 7/9, St. Petersburg 199034, Russia

Click-like condensation of boronic acids with specifically designed triols (boronate-triol coupling) produces stable diamantane adducts in aqueous medium, which can be controllably cleaved to initial components under acidic conditions or by using boric acid as a chemical trigger. This novel “click-declick” strategy allows for the creation of temporary covalent connections between two or more modular units, which was demonstrated by the synthesis of new fluorophore-labeled natural molecules (peptides, steroids), supramolecular assemblies, modified polymers, boronic acid scavengers, solid-supported organocatalysts, biodegradable COF-like materials, and dynamic combinatorial libraries.

Golovanov I.S. , Mazeina G.S. , Nelyubina Y.V. , Novikov R.A. , Mazur A.S. , Britvin S.N. , Tartakovsky V.A. , Ioffe S.L. , Sukhorukov A.Y.
Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent “Click-Declick” Chemistry
Journal of Organic Chemistry. 2018. V.83. N17. P.9756-9773. DOI: 10.1021/acs.joc.8b01296 WOS Scopus OpenAlex

Web of science:	WOS:000444364600016
Scopus:	2-s2.0-85052327261
OpenAlex:	W2886965895

БД	Цитирований
OpenAlex	30
Scopus	22
Web of science	22