Synthetic Methods for Heterocycles and Carbocycles Bearing Fluorinated One-Carbon Units (=CF&lt;sub&gt;2&lt;/sub&gt;, CHF&lt;sub&gt;2&lt;/sub&gt;, or CF&lt;sub&gt;3&lt;/sub&gt;): Intramolecular Reaction of 2-Trifluoromethyl-1-alkenes

Ichikawa, Junji

doi:10.5059/yukigoseikyokaishi.68.1175

Cited by 53 publications

(5 citation statements)

References 128 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As shown in Scheme 8, Ichikawa employed a dehydrogenation treatment of dihydroisoquinoline 22 to achieve the 4-trifluoromethylisoquinoline 23 in high yield. The same substrate was subjected to dehydrofluorination (with subsequent alkene isomerization) to obtain 4-difluoromethylisoquinoline 24 in good yield [31].…”

Section: Preparation Of Selectively Trifluoromethylated and Difluorommentioning

confidence: 99%

Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress

Sloop

2017

Journal of Chemistry

View full text Add to dashboard Cite

Heterocyclic molecules incorporating fluorinated isoquinoline components are found in many medicinally and agriculturally important bioactive products as well as industrially impactful materials. Within the past decade, a variety of isoquinolinic ring assembly techniques has enabled the introduction of diverse fluorine-containing functionalities which can enhance potential bioactivity and industrial utility. This review examines recent noncatalyzed and transition metal catalyzed synthetic approaches to the assembly of isoquinoline derivatives that are ring-fluorinated and/or result in the incorporation of fluorine-containing functional groups. Specifically, efficient synthetic methods and regioselectivity in the incorporation of functional groups into isoquinoline ring systems are examined.

show abstract

Section: Preparation Of Selectively Trifluoromethylated and Difluorommentioning

confidence: 99%

Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress

Sloop

2017

Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Previously, we have developed an alternative approach to obtain ring-fluorinated heterocycles through the intramolecular cyclization of fluoroalkenes, which simultaneously induced the construction of heterocycle skeletons and regioselective installation of the fluorine substituents. [1,[15][16][17][18][19][20][21][22][23][24] We achieved 5endo-trig cyclization of the β,β-difluorostyrene bearing a hydroxy group at the ortho-position, which leads to the synthesis of 3-alkylated 2-fluorobenzofuran (Scheme 1,a) [20,21] . Although 5-endo-trig cyclization is considered to be difficult according to Baldwin's rules [25 -35] , this type of cyclization is enabled by the abnormally polarized double bonds in difluoroalkenes.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 2‐Fluorobenzofurans: 5‐endo‐trig Cyclization of β,β‐Difluoro‐o‐hydroxystyrenes

Morioka

Fujita

Ichikawa

2020

Helvetica Chimica Acta

Self Cite

View full text Add to dashboard Cite

Dedicated to Professor Antonio Togni on the occasion of his 65th birthday Efficient synthetic methods were established for obtaining 2-fluorobenzofurans involving various substituents. Upon being treated with 1,8-diazabicyclo[5.4.0]undec-7-ene under microwave irradiation, the α-unsubstituted β,β-difluoro-o-hydroxystyrenes underwent nucleophilic 5-endo-trig cyclization to afford the corresponding 2fluorobenzofurans in high yields. Furthermore, 2-fluoro-3-iodobenzofuran was successfully synthesized, and its transformation to various 3-substituted 2-fluorobenzofurans was demonstrated.

show abstract

“…The 1,1-difluoroethenylidene functionality in these compounds is also known to act as a bioisostere for the carbonyl group of many biologically active compounds [9–12]. Although numerous methods for the preparation of 2,2-disubstituted-1,1-difluoroethenes have been reported in the previous literature [13–22], a consecutive cross-coupling reaction of a proper precursor such as a 1,1-difluoroethenylidene species bearing a metal functional group, a halogen substituent or a tosylate group at the vinyl carbon will provide a concise and efficient method for the synthesis of 2,2-disubstituted-1,1-difluoroethenes.…”

Section: Introductionmentioning

confidence: 99%

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

Kim

Choi

Jeong

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acids in the presence of catalytic amount of Pd(PPh3)2Cl2 and Na2CO3 in this reaction resulted in the formation of symmetrical di-coupled products 4 in high yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3.

show abstract

Synthetic Methods for Heterocycles and Carbocycles Bearing Fluorinated One-Carbon Units (=CF<sub>2</sub>, CHF<sub>2</sub>, or CF<sub>3</sub>): Intramolecular Reaction of 2-Trifluoromethyl-1-alkenes

Cited by 53 publications

References 128 publications

Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress

Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress

Facile Synthesis of 2‐Fluorobenzofurans: 5‐endo‐trig Cyclization of β,β‐Difluoro‐o‐hydroxystyrenes

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

Contact Info

Product

Resources

About