Tripleipso-defluoroetherification of (trifluoromethyl)alkenes with fluoroalkylated alcohols: access to fluoroalkylated orthoestersviaC(sp3)–F bond cleavage DOI

Jia Nie,

Huanfeng Jiang, Chuanle Zhu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(53), P. 8238 - 8241

Published: Jan. 1, 2023

The triple ipso-defluoroetherification of (trifluoromethyl)alkenes with fluoroalkylated alcohols by C(sp3)-F bond cleavage is reported, delivering various orthoesters in high yields. This reaction transition-metal free and gram-scalable, features mild conditions, tolerates diverse functional groups.

Language: Английский

Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds DOI

Jia‐Wei Liu,

Shiyu Li, Jun Xu

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(8)

Published: Dec. 28, 2023

Abstract The selective C−F bonds functionalization in available trifluoromethyl compounds is an economic route for obtaining high‐value organic fluorine compounds. However, due to the high dissociation energy group, strength of bond decreases continuously during defluorination, posing a challenge modifying such molecules without over‐conversion. Over past few years, there has been significant progress developing efficient methods constructing difluoromethylene unit, using approaches as radical chemistry, photochemistry, electrochemistry, and organometallic chemistry. These involve difluorocarbon radicals, cations, anions, carbenes intermediates. In this review, we summarized recent five years research achievements field single cleavage aromatic carbonyl gain diverse difluoromethylene‐containing via different intermediate strategies.

Language: Английский

Citations

7
Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines DOI

Kannika La‐ongthong,

Teera Chantarojsiri, Darunee Soorukram

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: March 16, 2024

A benign electrochemical method to access 6-methylphenanthridines from 2-isocyanobiaryls using N,N-dimethylformamide (DMF) as a methyl source is reported. The protocol operates at ambient temperature without the need for harmful methylating reagents. Mechanistic studies suggested that DMF delivered methylene synthon, followed by reduction cathode and tautomerization. offers environmental benefits avoiding metal-based reagents harsh conditions.

Language: Английский

Citations

2
Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition DOI
Weidi Zeng, Mingqiang Li,

Shaofeng Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3421 - 3426

Published: Jan. 1, 2024

The synthesis of gem -difluoro-1,5-dienes via regioselective S N 2′-type reactions alkylidene malonates with trifluoromethyl alkenes and their subsequent [2 + 2] photocycloaddition for the formation bicyclo[2.1.1]hexanes are described.

Language: Английский

Citations

2
Visible Light Induced Selective Cleavage of Single C(sp3)-F Bond in Trifluoromethyl Groups Containing Compounds DOI
Fang Wang,

Qidi Wang,

Lei Wang

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 163, P. 134155 - 134155

Published: July 16, 2024

Language: Английский

Citations

2
Tripleipso-defluoroetherification of (trifluoromethyl)alkenes with fluoroalkylated alcohols: access to fluoroalkylated orthoestersviaC(sp3)–F bond cleavage DOI

Jia Nie,

Huanfeng Jiang, Chuanle Zhu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(53), P. 8238 - 8241

Published: Jan. 1, 2023

The triple ipso-defluoroetherification of (trifluoromethyl)alkenes with fluoroalkylated alcohols by C(sp3)-F bond cleavage is reported, delivering various orthoesters in high yields. This reaction transition-metal free and gram-scalable, features mild conditions, tolerates diverse functional groups.

Language: Английский

Citations

6