Catalytic Stereoconvergent Synthesis of Homochiral β-CF3, β-SCF3, and β-OCF3 Benzylic Alcohols DOI Creative Commons
Andrej Emanuel Cotman, Pavel A. Dub, Maša Sterle

и другие.

ACS Organic & Inorganic Au, Год журнала: 2022, Номер 2(5), С. 396 - 404

Опубликована: Июнь 8, 2022

We describe an efficient catalytic strategy for enantio- and diastereoselective synthesis of homochiral β-CF3, β-SCF3, β-OCF3 benzylic alcohols. The approach is based on dynamic kinetic resolution (DKR) with Noyori-Ikariya asymmetric transfer hydrogenation leading to simultaneous construction two contiguous stereogenic centers up 99.9% ee, 99.9:0.1 dr, 99% isolated yield. origin the stereoselectivity racemization mechanism DKR rationalized by density functional theory calculations. Applicability previously inaccessible chiral fluorinated alcohols obtained this method in directions further demonstrated: As building blocks pharmaceuticals, illustrated heat shock protein 90 inhibitor vitro anticancer activity, particular, needle-shaped crystals representative stereopure products that exhibit either elastic or plastic flexibility, which opens door materials mechanically responsive molecular crystals.

Язык: Английский

Deep blue diboron embedded multi-resonance thermally activated delayed fluorescence emitters for narrowband organic light emitting diodes DOI
Kenkera Rayappa Naveen, Hyuna Lee, Ramanaskanda Braveenth

и другие.

Chemical Engineering Journal, Год журнала: 2021, Номер 432, С. 134381 - 134381

Опубликована: Дек. 30, 2021

Язык: Английский

Процитировано

95
Healing through Histidine: Bioinspired Pathways to Self-Healing Polymers via Imidazole–Metal Coordination DOI Creative Commons

Stefan Zechel,

Martin D. Hager, Tobias Priemel

и другие.

Biomimetics, Год журнала: 2019, Номер 4(1), С. 20 - 20

Опубликована: Фев. 27, 2019

Biology offers a valuable inspiration toward the development of self-healing engineering composites and polymers. In particular, chemical level design principles extracted from proteinaceous biopolymers, especially mussel byssus, provide for autonomous intrinsic healing in synthetic The byssus is an acellular tissue comprised extremely tough protein-based fibers, produced by mussels to secure attachment on rocky surfaces. Threads exhibit response following apparent plastic yield event, recovering initial material properties time-dependent fashion. Recent biochemical analysis structure–function relationships defining this reveal key role sacrificial cross-links based metal coordination bonds between Zn2+ ions histidine amino acid residues. Inspired example, many research groups have developed polymeric materials (imidazole)–metal chemistry. review, we detailed overview current understanding mechanism byssal threads, state art histidine- imidazole-based

Язык: Английский

Процитировано

80
PFAS use in electronic products and exposure risks during handling and processing of e-waste: A review DOI
Berrin Tansel

Journal of Environmental Management, Год журнала: 2022, Номер 316, С. 115291 - 115291

Опубликована: Май 15, 2022

Язык: Английский

Процитировано

62
The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine DOI Creative Commons
Qian Wang, Jianlin Han, Alexander E. Sorochinsky

и другие.

Pharmaceuticals, Год журнала: 2022, Номер 15(8), С. 999 - 999

Опубликована: Авг. 14, 2022

Nowadays, the selective introduction of fluorine into bioactive compounds is a mature strategy in design drugs allowing to increase efficiency, biological half-life and bio-absorption. On other hand, amino acids (AAs) represent one most ubiquitious classes naturally occurring organic compounds, which are found over 40% newly marked small-molecule pharmaceutical medical formulations. The primary goal this work underscore two major trends modern pharmaceuticals. first dealing with unique structural characteristics provided by structure featuring an abundance functionality presence stereogenic center, all bodes well for successful development targeted bioactivity. second related fine-tuning desired activity pharmacokinetics fluorine. Historically, both were developed separately as innovative prolific approaches drug design. However, recent decades, these clearly converging leading ever-increasing number approved pharmaceuticals containing features

Язык: Английский

Процитировано

43
New Approved Drugs Appearing in the Pharmaceutical Market in 2022 Featuring Fragments of Tailor-Made Amino Acids and Fluorine DOI Creative Commons
Nana Wang, Haibo Mei, Gagan Dhawan

и другие.

Molecules, Год журнала: 2023, Номер 28(9), С. 3651 - 3651

Опубликована: Апрель 22, 2023

The strategic fluorination of oxidatively vulnerable sites in bioactive compounds is a relatively recent, widely used approach allowing us to modulate the stability, bio-absorption, and overall efficiency pharmaceutical drugs. On other hand, natural tailor-made amino acids are traditionally as basic scaffolds for development molecules. main goal this review article emphasize these general trends featured recently approved

Язык: Английский

Процитировано

30
Applications of Transition Metal-Catalyzed ortho-Fluorine-Directed C–H Functionalization of (Poly)fluoroarenes in Organic Synthesis DOI Creative Commons
Yudha P. Budiman, Robin N. Perutz, Patrick G. Steel

и другие.

Chemical Reviews, Год журнала: 2024, Номер 124(8), С. 4822 - 4862

Опубликована: Апрель 2, 2024

The synthesis of organic compounds efficiently via fewer steps but in higher yields is desirable as this reduces energy and reagent use, waste production, thus environmental impact well cost. reactivity C–H bonds ortho to fluorine substituents (poly)fluoroarenes with metal centers enhanced relative meta para positions. Thus, direct functionalization without prefunctionalization becoming a significant area research chemistry. Novel selective methodologies functionalize (poly)fluorinated arenes by taking advantage the C–F are continuously being developed. This review summarizes reasons for consequent developments valuable (poly)fluoroarene-containing compounds.

Язык: Английский

Процитировано

16
Direct and Chemoselective Synthesis of Tertiary Difluoroketones via Weinreb Amide Homologation with a CHF2-Carbene Equivalent DOI
Margherita Miele, Andrea Citarella, Nicola Micale

и другие.

Organic Letters, Год журнала: 2019, Номер 21(20), С. 8261 - 8265

Опубликована: Окт. 10, 2019

The homologation of Weinreb amides into difluoromethylketones with a formal nucleophilic CHF2 transfer agent is reported. Activating TMSCHF2 potassium tert-amylate enables convenient access to the difluorinated reagent, which adds acylating partners. high chemoselectivity showcased in presence variously multifunctionalized amides, jointly uniformly yields, strategy general applicability without requiring any stabilization element for putative carbanion.

Язык: Английский

Процитировано

69
Expanding organofluorine chemical space: the design of chiral fluorinated isosteres enabled by I(i)/I(iii) catalysis DOI Creative Commons

Stephanie Meyer,

Joel Häfliger, Ryan Gilmour

и другие.

Chemical Science, Год журнала: 2021, Номер 12(32), С. 10686 - 10695

Опубликована: Янв. 1, 2021

Short aliphatic groups are prevalent in bioactive small molecules and play an essential role regulating physicochemistry molecular recognition phenomena.

Язык: Английский

Процитировано

57
Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes DOI

Mélissa Cloutier,

Majdouline Roudias,

Jean‐François Paquin

и другие.

Organic Letters, Год журнала: 2019, Номер 21(10), С. 3866 - 3870

Опубликована: Апрель 30, 2019

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. corresponding trifluoromethylated pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use CF3 SF5 highly efficient directing groups this reaction. Notably, transformation represents first gold catalysis.

Язык: Английский

Процитировано

56
Recent Progress in the Design of Fused-Ring Non-Fullerene Acceptors─Relations between Molecular Structure and Optical, Electronic, and Photovoltaic Properties DOI Creative Commons

Bettina Schweda,

Matiss Reinfelds,

Petra Hofstadler

и другие.

ACS Applied Energy Materials, Год журнала: 2021, Номер 4(11), С. 11899 - 11981

Опубликована: Окт. 26, 2021

Organic solar cells are on the dawn of next era. The change focus toward non-fullerene acceptors has introduced an enormous amount organic n-type materials and drastically increased power conversion efficiencies photovoltaics, now exceeding 18%, a value that was believed to be unreachable some years ago. In this Review, we summarize recent progress in design ladder-type fused-ring 2018–2020. We thereby concentrate single layer heterojunction omit tandem architectures as well ternary cells. By analyzing more than 700 structures, highlight basic principles their influence optical electrical structure acceptor molecules review photovoltaic performance obtained so far. This Review should give extensive overview plenitude motifs but will also help understand which structures strategies beneficial for designing highly efficient

Язык: Английский

Процитировано

55