Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines DOI

Jiyuan Lyu,

Aurélie Claraz, Maxime R. Vitale

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(20), P. 12843 - 12855

Published: Sept. 21, 2020

Chiral phosphoric acid based organocatalysis and visible-light photocatalysis have both emerged as promising technologies for the sustainable production of fine chemicals. In this context, we envisioned design synthesis a new class chimeric catalytic entities that would feature capabilities. Given their multitask nature, such catalysts be particularly attractive development transformations, tandem processes in particular. Toward goal, several BINOL-based chiral backbones presenting one or two visible-light-sensitive thioxanthone moieties been prepared studied. The utility these photoactive organocatalysts is then demonstrated enantioselective three-component electrophilic amination enecarbamates. Of note, C1-symmetric organo/photocatalyst has shown better activity than those C2 symmetry.

Language: Английский

Cooperative Stereoinduction in Asymmetric Photocatalysis DOI
Steven J. Chapman, Wesley B. Swords, Christine M. Le

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(9), P. 4206 - 4213

Published: Feb. 22, 2022

Stereoinduction in complex organic reactions often involves the influence of multiple stereocontrol elements. The interaction among these can result observation significant cooperative effects that afford different rates and selectivities between matched mismatched sets stereodifferentiating chiral elucidation matched/mismatched ground-state chemical was a critically important theme maturation modern stereocontrolled synthesis. development robust methods for control photochemical reactions, however, is relatively recent development, similar stereocontrolling excited-state enantioselective photoreactions have not previously been documented. Herein, we describe tandem photocatalyst/Brønsted acid strategy highly [2 + 2] photocycloadditions vinylpyridines. Importantly, catalyst pairs exhibit reaction enantioselectivities across range coupling partners. We observe no evidence interactions catalysts conclude arise from their behavior transient assembly. These results suggest might be other classes dual-catalytic reactions.

Language: Английский

Citations

32

Ion-Pairing Catalysis in Stereoselective, Light-Induced Transformations DOI

Tobias E. Schirmer,

Burkhard König

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(42), P. 19207 - 19218

Published: Oct. 14, 2022

With the rapid development of photoredox catalysis, numerous concepts for asymmetric induction were successfully and broadly adapted from polar two-electron transformations to radical chemistry. While this applies organocatalysis or transition metal chemistry, ion-pairing catalysis remains a niche application within light-driven reactions today. This perspective gives an overview recent examples, strategies, their in stereoselective at interface photo(redox) catalysis.

Language: Английский

Citations

32

Photobiocatalysis in Continuous Flow DOI Creative Commons
Santiago Nahuel Chanquia, Alessia Valotta, Heidrun Gruber‐Wölfler

et al.

Frontiers in Catalysis, Journal Year: 2022, Volume and Issue: 1

Published: Jan. 10, 2022

In the last years, there were two fields that experienced an astonishing growth within biocatalysis community: photobiocatalysis and applications of flow technology to catalytic processes. Therefore, it is not a surprise combination these research areas also gave place several recent interesting articles. However, best our knowledge, no review article covering advances was published so far. Within this review, we present very developments in field continuous flow, discuss different practical features state-of-the art photobioreactors lastly, some future perspectives field.

Language: Английский

Citations

30

Visible light mediated functionalization of allenes DOI
Jitender Singh, Anoop Sharma, Anuj Sharma

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(20), P. 5651 - 5667

Published: Jan. 1, 2021

This review summarizes the visible light mediated strategies for functionalization of allenes.

Language: Английский

Citations

36

Nickel‐Mediated Enantioselective Photoredox Allylation of Aldehydes with Visible Light DOI
Francesco Calogero, Simone Potenti, Elena Bassan

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(11)

Published: Dec. 22, 2021

Here we report a practical, highly enantioselective photoredox allylation of aldehydes mediated by chiral nickel complexes with commercially available allyl acetate as the allylating agent. The methodology allows clean stereoselective in good to excellent yields and up 93 % e.e. using catalytic amount NiCl2 (glyme) presence aminoindanol-derived bis(oxazoline) ligand. system is constituted organic dye 3DPAFIPN Hantzsch's ester sacrificial reductant. reaction proceeds under visible-light irradiation (blue LEDs, 456 nm) at 8-12 °C. Compared other published procedures, no metal reductants (such Zn or Mn), additives (e.g. CuI) air-sensitive Ni(COD)2 are necessary for this reaction. Accurate DFT calculations photophysical experiments have clarified mechanistic picture

Language: Английский

Citations

36

Coupling light with biocatalysis for sustainable synthesis—very recent developments and future perspectives DOI Creative Commons
Lars‐Erik Meyer, Bekir Engin Eser, Selin Kara

et al.

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2021, Volume and Issue: 31, P. 100496 - 100496

Published: April 22, 2021

Using light for biocatalysis is a relatively new and expanding research field. Because of the ever-increasing number publications, this review highlights developments in field photobiocatalysis published past two years. We introduce topic briefly list most articles appeared so far. Afterward, we devote special attention to interesting relevant key vitro photobiocatalysis, briefly, describe novel discoveries photobiocatalytic cascades strict light-dependent enzymes. Finally, outline next decade conclusions future perspectives part.

Language: Английский

Citations

35

Recent Advances in Visible Light‐induced Asymmetric Transformations of Carbonyl Compounds into Chiral Alcohols DOI
Liuzhen Hou, Xiaohua Liu, Weidi Cao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(21)

Published: Aug. 16, 2023

Abstract Visible light‐induced photocatalysis has been widely investigated, which offers exciting opportunities to build new catalytic platforms that are unattainable under ground state conditions. Asymmetric a longstanding challenge due the high reactivity of photogenerated intermediates leading strong background reaction. Carbonyl group is an important fundamental scaffold in organic synthesis. The photocatalytic asymmetric transformations carbonyl compounds for synthesizing enantioenriched secondary and tertiary alcohols significant value but remain problematic. Even so, series intriguing works concerning this topic have reported recent year. This review summarizes advances area, mainly dividing into single synergetic catalyst systems, mechanism each reaction discussed.

Language: Английский

Citations

16

Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade toward β-gem-dihalovinyl carbonyls DOI
Dan Wu, Wen‐Juan Hao,

Qian Rao

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(15), P. 1911 - 1914

Published: Jan. 1, 2021

A new and general photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade of 1,7-diynes with alkyl halides such as BrCCl3and CBr4was reported for the first time, producing 65 hitherto unreported β-gem-dihalovinyl ketones/aldehydes moderate to excellent yields.

Language: Английский

Citations

27

Enantioselective Hydroalkylation of Alkenylpyridines Enabled by Merging Photoactive Electron Donor–Acceptor Complexes with Chiral Bifunctional Organocatalysis DOI
Jing Guo, Ying Xie,

Zemin Lai

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(20), P. 13065 - 13074

Published: Oct. 12, 2022

The potential of electron donor–acceptor (EDA) complex photochemistry has recently been recognized in visible-light-induced photocatalyst-free radical reactions. design catalytic asymmetric reactions driven by EDA complexes remains a substantial challenge, and existing examples are limited to sole activation modes with aminocatalysts or phase-transfer catalysts. Herein, we demonstrate that chiral bifunctional hydrogen-bonding catalysis can realize the reaction an via dual afford vicinal tertiary stereocenters at β,γ-positions pyridines high yields good enantio- diastereoselectivities. Mechanistic studies suggest crucial success factor for this transformation is use phosphoric acid (CPA), which not only accelerates situ formation aggregates between redox-active esters (RAEs) Hantzsch (HEs) but also provides proper substrate induction.

Language: Английский

Citations

22

Photocatalytic asymmetric cross-dehydrogenative coupling of tetrahydroisoquinoline scaffolds DOI
Biplob Borah, L. Raju Chowhan

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155630 - 155630

Published: April 1, 2025

Language: Английский

Citations

0