scholarly journals Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

2021 ◽  
Vol 14 (7) ◽  
pp. 661
Author(s):  
Thierry Besson ◽  
Corinne Fruit
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Heterocyclic Compounds ◽  
Environmentally Friendly ◽  
Direct Arylation ◽  
Stepping Stone ◽  
Metal Free ◽  
Bond Forming ◽  
Diaryliodonium Salts ◽  
Recent Advances

Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

scholarly journals Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guogang Deng ◽  
Shengzu Duan ◽  
Jing Wang ◽  
Zhuo Chen ◽  
Tongqi Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allyl Ether ◽  
Metal Catalyst ◽  
Metal Free ◽  
Allyl Ethers ◽  
Bond Forming ◽  
Allyl Halides ◽  
Synthetic Utility ◽  
Insight Into ◽  
Allyl Esters

AbstractAllylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

Novel Naproxen Derivatives: Lewis Acid/Transition-metal Free Synthesis via C-C Bond Forming Reaction

2007 ◽  
Vol 4 (4) ◽  
pp. 292-295 ◽  
Author(s):  
Sarbani Pal ◽  
P. Bindu ◽  
Pragnyadhar Reddy Venna ◽  
P. K. Dubey
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Metal Free ◽  
Bond Forming

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Synthesis ◽  
2021 ◽  
Author(s):  
Leonid Fershtat ◽  
Fedor Teslenko
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
State Of The Art ◽  
Short Review ◽  
Advanced Materials ◽  
Metal Free ◽  
Recent Advances ◽  
Application Potential ◽  
Metal Catalyzed

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

Transition Metal-Free O-Arylation of Quinoxalin-2-ones with Diaryliodonium Salts

Heterocycles ◽  
2021 ◽  
Vol 103 (1) ◽  
pp. 502
Author(s):  
Masami Kuriyama ◽  
Osamu Onomura ◽  
Yuki Mochizuki ◽  
Tsubasa Miyagi ◽  
Kosuke Yamamoto ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Diaryliodonium Salts

Transition metal-free base-promoted arylation of sulfenate anions with diaryliodonium salts

2019 ◽  
Vol 6 (1) ◽  
pp. 32-35 ◽  
Author(s):  
Lei Wang ◽  
Mingjie Chen ◽  
Junliang Zhang
Keyword(s):  
Transition Metal ◽  
Free Base ◽  
Metal Free ◽  
Diaryliodonium Salts

A base-promoted formal arylation of general sulfenate anions with diaryliodonium salts under transition-metal-free conditions has been described.

Sign in / Sign up

Export Citation Format

Share Document