Visible-light photoredox synthesis of internal alkynes containing quaternary carbons

2016 ◽  
Vol 52 (45) ◽  
pp. 7292-7294 ◽  
Author(s):  
Chang Gao ◽  
Jingjing Li ◽  
Jipan Yu ◽  
Haijun Yang ◽  
Hua Fu
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Coupling Reactions ◽  
Internal Alkynes ◽  
Quaternary Carbons

A novel and efficient visible-light photoredox method for the synthesis of internal alkynes containing quaternary carbons has been developed via coupling reactions of N-phthalimidoyl oxalates of tert-alcohols with 1-(2-(arylsulfonyl)ethynyl)benzenes. The reactions proceeded well at room temperature with good functional group tolerability.

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Room Temperature ◽  
Functional Group ◽  
Ammonium Thiocyanate ◽  
Potassium Persulfate ◽  
Sulfur Source ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Metal Free

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.

ChemInform Abstract: Visible-Light Photoredox Synthesis of Internal Alkynes Containing Quaternary Carbons.

ChemInform ◽  
2016 ◽  
Vol 47 (40) ◽  
Author(s):  
Chang Gao ◽  
Jingjing Li ◽  
Jipan Yu ◽  
Haijun Yang ◽  
Hua Fu
Keyword(s):  
Visible Light ◽  
Internal Alkynes ◽  
Quaternary Carbons

scholarly journals Catalytic Asymmetric Allylation of Aldehydes with Alkenes Mediated by Organophotoredox and Chiral Chromium Hybrid Catalysis

2018 ◽  
Author(s):  
Harunobu Mitsunuma ◽  
Shun Tanabe ◽  
Hiromu Fuse ◽  
Kei Ohkubo ◽  
Motomu Kanai
Keyword(s):  
Visible Light ◽  
Hybrid System ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Functional Group ◽  
Light Irradiation ◽  
Asymmetric Allylation ◽  
Complex Catalyst ◽  
Homoallylic Alcohols ◽  
Catalytic Asymmetric

A hybrid system accomplishing cooperativity between an organophotoredox acridinium catalyst and a chiral chromium<br>complex catalyst was developed, enabling the unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for the asymmetric allylation of aldehydes. The reaction proceeded under visible light irradiation at room temperature and with high functional group tolerance, affording the corresponding homoallylic alcohols with up to >20/1 diastereomeric ratio and 99% ee. The addition of Mg(ClO4)2 elicited profound enhancement of both reactivity and enantioselectivity.

Anionic Cyclometallated platinum(II) Tetrazolato Complexes as Viable Photoredox Catalysts

2018 ◽  
Author(s):  
Anna Maria Ranieri ◽  
Liam Burt ◽  
Stefano Stagni ◽  
Stefano Zacchini ◽  
Brian Skelton ◽  
...  
Keyword(s):  
Solid State ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Photophysical Properties ◽  
General Structure ◽  
No Emission ◽  
Michael Acceptors ◽  
Catalyzed Reactions

The synthesis, characterization, photophysical and photocatalytic studies of anionic platinum(II) tetrazolato complexes, with the general structure [TBA][Pt(CNC)TzR], are reported, where CNC<sup>2-</sup>represents a doubly cyclometalated 2,4,6-triphenylpyridine, TzR<sup>- </sup>is an anionic 5-substituted tetrazolato ligand (with a variable R functional group) and TBA<sup>+ </sup>is the tetrabutylammonium countercation. The complexes were prepared by substitution of the DMSO ligand in [Pt(CNC)(DMSO)] with the corresponding tetrazolato ligand. No emission from the platinum(II) complexes was detected at room temperature in solution, but the photophysical properties could be assessed in the solid state, where all the complexes display emission bands attributed to aggregates. The platinum(II) complexes were found to facilitate a range of fundamental classes of visible-light-mediated photoredox-catalyzed reactions, including α‑amino C–H functionalization processes, such as Povarov-type reactions and the addition of α-amino C–H bonds across Michael acceptors, in addition to ATRA chemistry, and a hydrodeiodination. With the exception of the hydrodeiodination process, the best Pt(II) catalysts provided turnover numbers of 150–175 in each of these transformations.

P2Et Phosphazene: A Mild, Functional Group Tolerant Base for Soluble, Room Temperature Pd-Catalyzed C–N, C–O, and C–C Cross-Coupling Reactions

2015 ◽  
Vol 17 (13) ◽  
pp. 3370-3373 ◽  
Author(s):  
Alexander Buitrago Santanilla ◽  
Melodie Christensen ◽  
Louis-Charles Campeau ◽  
Ian W. Davies ◽  
Spencer D. Dreher
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Visible-light-promoted selective C–H amination of heteroarenes with heteroaromatic amines under metal-free conditions

2017 ◽  
Vol 15 (45) ◽  
pp. 9590-9594 ◽  
Author(s):  
Supravat Samanta ◽  
Chitrakar Ravi ◽  
Sadu Nageswara Rao ◽  
Abhisek Joshi ◽  
Subbarayappa Adimurthy
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Metal Free ◽  
High Degree

The regioselective C–H amination of quinoline amides (C5) and imidazopyridines (C3) under transition-metal-free conditions at room temperature with a high degree of functional group tolerance is reported.

scholarly journals g-C3N4/γ-Fe2O3/TiO2/Pd: a new magnetically separable photocatalyst for visible-light-driven fluoride-free Hiyama and Suzuki–Miyaura cross-coupling reactions at room temperature

2020 ◽  
Vol 44 (27) ◽  
pp. 11513-11526 ◽  
Author(s):  
Roya Jahanshahi ◽  
Asma Khazaee ◽  
Sara Sobhani ◽  
José Miguel Sansano
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Cross Coupling ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven ◽  
Magnetically Separable

g-C3N4/γ-Fe2O3/TiO2/Pd is developed as a new magnetically separable photocatalyst for efficient fluoride-free Hiyama and Suzuki–Miyaura cross-coupling reactions at room temperature under visible light irradiation.

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)–C(sp) bond formation catalyzed by a B12 complex

2019 ◽  
Vol 55 (87) ◽  
pp. 13070-13073 ◽  
Author(s):  
Li Chen ◽  
Yohei Kametani ◽  
Kenji Imamura ◽  
Tsukasa Abe ◽  
Yoshihito Shiota ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported.

scholarly journals Catalytic Asymmetric Allylation of Aldehydes with Alkenes Mediated by Organophotoredox and Chiral Chromium Hybrid Catalysis

2018 ◽  
Author(s):  
Harunobu Mitsunuma ◽  
Shun Tanabe ◽  
Hiromu Fuse ◽  
Kei Ohkubo ◽  
Motomu Kanai
Keyword(s):  
Visible Light ◽  
Hybrid System ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Functional Group ◽  
Light Irradiation ◽  
Asymmetric Allylation ◽  
Complex Catalyst ◽  
Homoallylic Alcohols ◽  
Catalytic Asymmetric

A hybrid system accomplishing cooperativity between an organophotoredox acridinium catalyst and a chiral chromium<br>complex catalyst was developed, enabling the unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for the asymmetric allylation of aldehydes. The reaction proceeded under visible light irradiation at room temperature and with high functional group tolerance, affording the corresponding homoallylic alcohols with up to >20/1 diastereomeric ratio and 99% ee. The addition of Mg(ClO4)2 elicited profound enhancement of both reactivity and enantioselectivity.

Aggregates of the pentacenequinone derivative as reactors for the preparation of Ag@Cu2O core–shell NPs: an active photocatalyst for Suzuki and Suzuki type coupling reactions

2015 ◽  
Vol 51 (63) ◽  
pp. 12529-12532 ◽  
Author(s):  
Kamaldeep Sharma ◽  
Manoj Kumar ◽  
Vandana Bhalla
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Light Harvesting ◽  
Cross Coupling ◽  
Core Shell ◽  
Coupling Reactions ◽  
Shell Nanoparticles ◽  
Cross Coupling Reactions ◽  
Type Coupling ◽  
Core Shell Nanoparticles

Aggregates of the pentacenequinone derivative stabilized Ag@Cu2O core–shell nanoparticles (NPs) enabled efficient visible light harvesting to catalyse the palladium free Suzuki–Miyaura and Suzuki type cross coupling reactions at room temperature.

Sign in / Sign up

Export Citation Format

Share Document