Photoinduced Three-Component Carboarylation of Unactivated Alkenes with Protic C(sp 3 )–H Feedstocks

et al. 2023

Org. Chem. Front.

“…Based on these experimental results and related literature, 7–13,16 a proposed mechanism is shown in Fig. 3.…”

Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent

Shen

et al. 2023

Org. Chem. Front.

“…For similar alkene difunctionalization reactions, [101] photo-induced multicomponent bifunctionalization of unactivated alkenes were also developed through decyanative strategy by the Lin group [102] and Deng group, [103] respectively (Scheme 29). In Lin's work, arylsilylation of alkenes under a transition-metal free with visible-light irradiation was realized by photoredox and HAT catalysis, this methodology offered a rapid strategy to silicon-containing complex compounds with wide substrate scope and good functional group tolerance.…”

Section: Photo-redox Catalyzed Radical Decyanative Arylation Enabled ...mentioning

confidence: 99%

Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies

Huang

2023

Adv Synth Catal

Decyanation is an important process in the synthesis of aromatic molecules in the studies of pharmaceutical research, medical and materials sciences. In late‐stage modifications of privileged carbo/heterocyclic scaffolds, radical‐type decyanation techniques have been devised to date. As a result, the chemistry of cyano‐involved conversions, a hotly debated subject over the past few decades, has advanced significantly. The cyano group (CN), on the other hand, has rarely been acknowledged as a good reaction site due to its thermodynamic robustness. The most recent advancements in catalytic radical decyanation protocols that CN behaved as a leaving group has made are surveyed in this article. Following the introduction of a number of different reaction modes, the catalytic reactions that are used to activate the C−CN bonds are primarily categorized, and the text herein are divided into three groups: (1) photo‐catalyzed decyanation transformations, (2) electro‐catalyzed decyanation transformations, and (3) transition‐metal‐catalyzed or metal‐free decyanation transformations. With an emphasis on the catalytic systems and synthetic applications in C−CN bond activation, this review will provide the readers with an overview of decyanation chemistry in radical reactions.

“…Continuing our interest in visible-light-induced alkylation reactions, herein, we report a mild protocol of visible-light-induced bromoallylation and alkylation of BCBs in a metal- and additive-free manner. The 2-isopropylthioxanthone catalyst plays different roles in this photoinduced divergent functionalization of BCBs.…”

mentioning

confidence: 99%

2-Isopropylthioxanthone-Catalyzed Divergent Functionalization of Bicyclo[1.1.0]butanes under Visible-Light Irradiation

et al. 2023

Org. Lett.

Self Cite

1,3-Functionalized cyclobutane structural motifs are ubiquitous in natural products and pharmaceuticals. Photoinduced alkylation of bicyclo[1.1.0]butanes (BCBs) offers a step-economical strategy for accessing 1,3-functionalized cyclobutane motifs. Herein, we disclose a general and mild photocatalytic protocol of bromoallylation and alkylation of BCBs in a metal, additive-free manner by using the same photocatalyst, 2-isopropylthioxanthone, in different catalytic roles. Furthermore, the synthetic utility of these products was illustrated in the synthesis of various valuable and complex cyclobutane derivatives.