Recent Progress in Transition-Metal-Free, Base-Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

2018 ◽  
Vol 7 (6) ◽  
pp. 985-1005 ◽  
Author(s):  
Tej Narayan Poudel ◽  
Ramuel John Inductivo Tamargo ◽  
Hongyun Cai ◽  
Yong Rok Lee
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Free Base ◽  
Diverse Range ◽  
Heteroaromatic Compounds ◽  
Metal Free

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

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.

Transition Metal‐Free, Base‐Induced Arylation of Amino Acids: Synthesis of N ‐( para ‐Substituted phenyl)amino‐2‐carboxylic acids

2020 ◽  
Vol 5 (28) ◽  
pp. 8644-8648 ◽  
Author(s):  
Adejoke D. Osinubi ◽  
Josephat U. Izunobi ◽  
Olayinka T. Asekun ◽  
Oluwole B. Familoni ◽  
Xiaoguang Bao
Keyword(s):  
Amino Acids ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Free Base ◽  
Metal Free

One-pot transition-metal-free cascade synthesis of thieno[2,3-c]coumarins from chromones

RSC Advances ◽  
2016 ◽  
Vol 6 (106) ◽  
pp. 103895-103898 ◽  
Author(s):  
Yuhong Yang ◽  
Xueyu Qi ◽  
Ruiling Liu ◽  
Qian He ◽  
Chunhao Yang
Keyword(s):  
Transition Metal ◽  
Cascade Reaction ◽  
Free Base ◽  
One Pot ◽  
Metal Free

A one-pot transition-metal-free, base-mediated synthesis of a novel series of functionalized thieno[2,3-c]coumarins has been developed through a cascade reaction from chromones.

Metal-Free Catalytic Aromatic C–H Borylation

Synlett ◽  
2020 ◽  
Vol 31 (19) ◽  
pp. 1857-1861
Author(s):  
Hua Zhang ◽  
Li Wang
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Rapid Development ◽  
Transition Metal Catalysis ◽  
Mechanistic Studies ◽  
Metal Catalysis ◽  
Promising Alternative ◽  
Metal Free ◽  
History Of ◽  
Near Future

In recent decades, C–H borylation has undergone rapid development and has become one of the most important and efficient methods for the synthesis of organoboron compounds. Although transition-metal catalysis dominates C–H borylation, the metal-free approach has emerged as a promising alternative strategy. This article briefly summarizes the history of metal-free aromatic C–H borylation, including early reports on electrophilic C–H borylation and recent progress in metal-free catalytic intermolecular C–H borylation; it also highlights our recent work on BF3·Et2O-catalyzed C2–H borylation of hetarenes. Despite these recent advances, comprehensive mechanistic studies on various metal-free catalytic aromatic C–H borylations and novel processes with a wider substrate scope are eagerly expected in the near future.

scholarly journals Recent progress in transition-metal-free functionalization of allenamides

RSC Advances ◽  
2020 ◽  
Vol 10 (60) ◽  
pp. 36818-36827
Author(s):  
Xiaoxiao Li ◽  
Yongchun Liu ◽  
Na Ding ◽  
Xiaoju Tan ◽  
Zhigang Zhao
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Complex Molecules ◽  
Metal Free ◽  
Powerful Approach

Recent progress in transition-metal-free functionalization of allenamides is reviewed, providing a powerful approach to rapidly access complex molecules.

Transition-Metal-Free Oxidation of Benzylic C–H Bonds of Six-Membered N-Heteroaromatic Compounds

2019 ◽  
Vol 84 (7) ◽  
pp. 4040-4049 ◽  
Author(s):  
Xianying Gao ◽  
Shuaijun Han ◽  
Maolin Zheng ◽  
Apeng Liang ◽  
Jingya Li ◽  
...  
Keyword(s):  
Transition Metal ◽  
Heteroaromatic Compounds ◽  
Metal Free ◽  
Free Oxidation

Uncovering Multifaceted Iodonium Ylides: Versatile Reactivity Enables Cyclization of Simple Arylamines

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2337-2341 ◽  
Author(s):  
Yao Wang ◽  
Liang Zhang
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Chemical Properties ◽  
Historical Background ◽  
Chemical Transformations ◽  
Metal Free ◽  
Reaction Discovery ◽  
Iodonium Ylides

Iodonium ylides can undergo cyclization with a simple tertiary arylamine to afford N-heterocyclic products in a transition-metal-free approach in the absence of an additional initiator/oxidant. The ­inherent reactivity uncovered in this transformation is fundamentally different from known chemical properties of iodonium ylide compounds, thus providing a new opportunity for the further exploration of iodonium ylide-based chemical transformations. This Synpacts article describes the historical background of iodonium ylide chemistry and highlights recent progress disclosed by our work.1 Introduction2 The Strategy for New Reaction Discovery3 Application to Cyclization of Tertiary Arylamines4 Conclusion and Perspectives

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