scholarly journals Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis

2012 ◽  
Vol 134 (19) ◽  
pp. 8094-8097 ◽  
Author(s):  
Daniel A. DiRocco ◽  
Tomislav Rovis
Keyword(s):  
Tertiary Amines ◽  
Photoredox Catalysis ◽  
Dual Catalysis ◽  
Catalytic Asymmetric

Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones

2017 ◽  
Vol 19 (8) ◽  
pp. 2122-2125 ◽  
Author(s):  
Niankai Fu ◽  
Longji Li ◽  
Qi Yang ◽  
Sanzhong Luo
Keyword(s):  
Oxidative Coupling ◽  
Tertiary Amines ◽  
Catalytic Asymmetric

scholarly journals Visible-light-driven spirocyclization of epoxides via dual titanocene and photoredox catalysis

2020 ◽  
Vol 11 (3) ◽  
pp. 839-844 ◽  
Author(s):  
Shuangjie Lin ◽  
Yuqing Chen ◽  
Fusheng Li ◽  
Caizhe Shi ◽  
Lei Shi
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Visible Light Driven ◽  
Dual Catalysis

We describe the synergistic utilization of titanocene/photoredox dual catalysis driven by visible light for radical opening/spirocyclization of easily accessible epoxyalkynes.

ChemInform Abstract: The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis.

ChemInform ◽  
2015 ◽  
Vol 46 (5) ◽  
pp. no-no
Author(s):  
Xiaojun Dai ◽  
Dongping Cheng ◽  
Baochuan Guan ◽  
Wenjuan Mao ◽  
Xiaoliang Xu ◽  
...  
Keyword(s):  
Visible Light ◽  
Tertiary Amines ◽  
Photoredox Catalysis

scholarly journals Decarboxylative 1,4-Carbocyanation of 1,3-Enynes to Access Tetra-substituted Allenes via Copper/Photoredox Dual Catalysis

2021 ◽  
Author(s):  
Ya Chen ◽  
Junjie Wang ◽  
Yixin Lu
Keyword(s):  
Copper Catalysis ◽  
Photoredox Catalysis ◽  
Dual Catalysis

We disclose herein the first example of merging photoredox catalysis and copper catalysis for radical 1,4-carbocyanations of 1,3-enynes. Alkyl N-hydroxyphthalimide esters are utilized as radical precusors, and the reported mild...

Photoredox Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zongbin Jia ◽  
Qi Yang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Tertiary Amines ◽  
Dehydrogenative Coupling ◽  
Cross Coupling Reaction ◽  
Iminium Ion ◽  
Amine Catalysis ◽  
Catalytic Asymmetric

We report herein a catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, following by isomerization, leading to aza-Morita-Baylis-Hillman-type products with good diastereo- and enantio- selectivity.

scholarly journals Anti-Markovnikov hydro(amino)alkylation of vinylarenes via photoredox catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhao Wu ◽  
Samuel N. Gockel ◽  
Kami L. Hull
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Alkyl Radical ◽  
Tertiary Amines ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Synthetic Utility ◽  
Powerful Means

AbstractPhotoredox catalysis is a powerful means to generate odd-electron species under mild reaction conditions from a wide array of radical precursors. Herein, we present the application of this powerful catalytic manifold to address the hydroalkylation and hydroaminoalkylation of electronically diverse vinylarenes. This reaction allows for generalized alkene hydroalkylation leveraging common alkyl radical precursors, such as organotrifluoroborate salts and carboxylic acids. Furthermore, utilizing easily accessible α-silyl amine reagents or tertiary amines directly, secondary and tertiary amine moieties can be installed onto monoaryl and diaryl alkenes to access valuable products, including γ,γ-diarylamines pharmacophores. Thus, under a unified system, both hydroalkylation and hydroaminoalkylation of alkenes are achieved. The substrate scope is evaluated through 57 examples, the synthetic utility of the method is demonstrated, and preliminary mechanistic insights are presented.

Visible Light Photoredox Catalysis: Investigation of Distalsp3CH Functionalization of Tertiary Amines for Alkylation Reaction

2014 ◽  
Vol 356 (13) ◽  
pp. 2813-2818 ◽  
Author(s):  
Ganesh Pandey ◽  
Deepak Jadhav ◽  
Sandip Kumar Tiwari ◽  
Bhawana Singh
Keyword(s):  
Visible Light ◽  
Alkylation Reaction ◽  
Tertiary Amines ◽  
Photoredox Catalysis

scholarly journals Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

2015 ◽  
Vol 11 ◽  
pp. 1570-1582 ◽  
Author(s):  
David W Manley ◽  
John C Walton
Keyword(s):  
Organic Synthesis ◽  
Radical Anion ◽  
Radical Cations ◽  
Aromatic Aldehydes ◽  
Hydrogen Gas ◽  
Primary Amines ◽  
Tertiary Amines ◽  
Photoredox Catalysis ◽  
Enol Ethers ◽  
Cyclic Amines

Heterogeneous semiconductor photoredox catalysis (SCPC), particularly with TiO2, is evolving to provide radically new synthetic applications. In this review we describe how photoactivated SCPCs can either (i) interact with a precursor that donates an electron to the semiconductor thus generating a radical cation; or (ii) interact with an acceptor precursor that picks up an electron with production of a radical anion. The radical cations of appropriate donors convert to neutral radicals usually by loss of a proton. The most efficient donors for synthetic purposes contain adjacent functional groups such that the neutral radicals are resonance stabilized. Thus, ET from allylic alkenes and enol ethers generated allyl type radicals that reacted with 1,2-diazine or imine co-reactants to yield functionalized hydrazones or benzylanilines. SCPC with tertiary amines enabled electron-deficient alkenes to be alkylated and furoquinolinones to be accessed. Primary amines on their own led to self-reactions involving C–N coupling and, with terminal diamines, cyclic amines were produced. Carboxylic acids were particularly fruitful affording C-centered radicals that alkylated alkenes and took part in tandem addition cyclizations producing chromenopyrroles; decarboxylative homo-dimerizations were also observed. Acceptors initially yielding radical anions included nitroaromatics and aromatic iodides. The latter led to hydrodehalogenations and cyclizations with suitable precursors. Reductive SCPC also enabled electron-deficient alkenes and aromatic aldehydes to be hydrogenated without the need for hydrogen gas.

scholarly journals Organic photoredox catalysis for the oxidation of silicates: applications in radical synthesis and dual catalysis

2016 ◽  
Vol 52 (64) ◽  
pp. 9877-9880 ◽  
Author(s):  
Christophe Lévêque ◽  
Ludwig Chenneberg ◽  
Vincent Corcé ◽  
Cyril Ollivier ◽  
Louis Fensterbank
Keyword(s):  
Organic Dye ◽  
Photoredox Catalysis ◽  
Alkyl Radicals ◽  
Metal Free ◽  
Dual Catalysis

Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals.

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