Reactivity and mechanistic insight into the cross coupling reaction between isochromans and β-keto esters through C–H bond activation under visible light irradiation

2016 ◽  
Vol 3 (4) ◽  
pp. 486-490 ◽  
Author(s):  
Ming Xiang ◽  
Qing-Yuan Meng ◽  
Xue-Wang Gao ◽  
Tao Lei ◽  
Bin Chen ◽  
...  
Keyword(s):  
Oxygen Atom ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Bond Activation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Keto Esters ◽  
Mechanistic Insight ◽  
Cross Coupling Reaction ◽  
Insight Into

The formation of a C(sp3)–C(sp3) bond next to an oxygen atom from two different C–H bonds is realized by oxidative photocatalysis.

Synthesis of aromatic β-keto esters via a carbonylative Suzuki–Miyaura coupling reaction of α-iodo esters with arylboronic acids

2015 ◽  
Vol 2 (9) ◽  
pp. 1085-1087 ◽  
Author(s):  
Shuhei Sumino ◽  
Takahito Ui ◽  
Ilhyong Ryu
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Amount ◽  
Pd Catalyst ◽  
Arylboronic Acids ◽  
Keto Esters ◽  
Cross Coupling Reaction ◽  
Alkyl Iodides

Aromatic β-keto esters were synthesized via a carbonylative cross-coupling reaction of alkyl iodides and arylboronic acids in the presence of a catalytic amount of Pd catalyst.

scholarly journals Design of a Multi-Use Photoreactor to Enable Visible Light Photocatalytic Chemical Transformations and Labeling in Live Cells

2020 ◽  
Author(s):  
Noah Bissonnette ◽  
Keun Ah Ryu ◽  
Tamara Reyes-Robles ◽  
Sharon Wilhelm ◽  
Erik Hett ◽  
...  
Keyword(s):  
Visible Light ◽  
Chemical Biology ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Live Cells ◽  
Chemical Transformations ◽  
Cross Coupling Reaction ◽  
Visible Light Driven ◽  
Visible Light Photocatalytic

<p>Despite the growing utilization of visible light photochemistry in both chemistry and biology, a general low-heat photoreactor for use across these different disciplines does not exist. Herein, we describe the design and utilization of a standardized photoreactor for visible light driven activation and photocatalytic chemical transformations. Using this single benchtop photoreactor, we perform photoredox reactions across multiple visible light wavelengths, a high throughput photocatalytic cross coupling reaction, and <i>in vitro</i> labeling of proteins and live cells. Given the success of this reactor in all tested applications, we envision that this multi-use photoreactor will be widely used in biology, chemical biology, and medicinal chemistry settings.</p>

Reactivity and Mechanistic Insight into Visible-Light-Induced Aerobic Cross-Dehydrogenative Coupling Reaction by Organophotocatalysts

2011 ◽  
Vol 18 (2) ◽  
pp. 620-627 ◽  
Author(s):  
Qiang Liu ◽  
Ya-Nan Li ◽  
Hui-Hui Zhang ◽  
Bin Chen ◽  
Chen-Ho Tung ◽  
...  
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Mechanistic Insight ◽  
Dehydrogenative Coupling ◽  
Insight Into

Synthesis of HIV NNRTI Doravirine Analogues via Visible-Light Photoredox Decarboxylative Cross-Coupling

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3177-3186
Author(s):  
Abdellatif ElMarrouni ◽  
Linda Suen ◽  
Cheng Wang ◽  
David Hunter ◽  
Helen Mitchell ◽  
...  
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Parallel Synthesis ◽  
Photoredox Catalysis ◽  
Broad Applicability ◽  
Cross Coupling Reaction ◽  
Clinical Candidate

A C(sp2)–C(sp3) decarboxylative cross-coupling reaction utilizing dual nickel and photoredox catalysis for rapid parallel synthesis of diverse C-ring analogues of the HIV NNRTI clinical candidate doravirine is developed and described herein. This protocol features an alkylation with readily available and inexpensive methyl bromoacetate followed by hydrolysis to prepare an advanced doravirine intermediate, which undergoes decarboxylative cross-coupling with a variety of aryl and heteroaryl bromides. The mildness, broad applicability, and sustainability of the current methodology are improvements over previously reported procedures and allow for rapid parallel synthesis of analogues. The optimization and scope of this method are reported.

Visible-light-activated copper(i) catalyzed oxidative Csp–Csp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base

2016 ◽  
Vol 18 (16) ◽  
pp. 4526-4530 ◽  
Author(s):  
Arunachalam Sagadevan ◽  
Ping-Chiang Lyu ◽  
Kuo Chu Hwang
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Efficient Synthesis ◽  
Cross Coupling Reaction ◽  
Conjugated Diynes

An efficient and eco-friendly approach to Csp–Csp cross-coupling of terminal alkynes for the construction of unsymmetrical conjugated diynes via a visible-light-induced CuCl catalysed process at room temperature is described.

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