Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)–O/C(sp2)–S Bond Cleavage Strategy

Synthesis ◽  
2021 ◽  
Author(s):  
Xin-Ge Yang ◽  
Xue-Qiang Wang ◽  
Shen-Huan Li ◽  
Cheng-Yu Long
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Aromatic Amines ◽  
Recent Progress ◽  
Bond Cleavage ◽  
Metal Free ◽  
Complementary Methods ◽  
The Past ◽  
Recent Advances ◽  
Metal Catalyzed

AbstractRecently, intense efforts have been dedicated to the development of novel synthetic strategies to access aromatic amines due to their importance in the pharmaceuticals, agrochemicals, materials, and natural product areas. Although numerous transition-metal-catalyzed C–N formation strategies have been described for the preparation of aromatic amines in the past few decades, complementary methods under transition-metal-free conditions are still required. We present the recent advances in the exploration of innovative amination approaches via C(sp2)–O/C(sp2)–S bond cleavage in this review.1 Introduction2 Stoichiometric Base-Promoted Amination3 Base-Catalyzed Amination4 Photoredox-Catalyzed Amination5 Acid-Promoted Amination6 Conclusion and Perspectives

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.

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

Synthesis ◽  
2021 ◽  
Author(s):  
sefa ucar ◽  
Arif Dastan
Keyword(s):  
Transition Metal ◽  
Comprehensive Overview ◽  
Metal Free ◽  
The Past ◽  
Recent Advances

Transition-metal-free arylation reactions have attracted considerable attention, because of economic and environmental reasons over the past 40 years. In recent years, in particular, many efforts have been made to develop efficient transition-metal-free approaches for the arylation of heteroarenes. Covering the literature from 2015 to early 2021, this review aims to provide a comprehensive overview of the synthetic and mechanistic aspects of these atom economical and environmentally harmless reactions. 1 Introduction 2 Arylation of Pre-functionalized Heteroarenes 3 Direct C-H Arylation of Heteroarenes 3.1 C(Sp2)-H Arylation 3.2 C(sp3)-H Arylation 4 N-Arylation of Heteroarenes 5 Summary and Outlook

Effective, transition metal free and selective C–F activation under mild conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (10) ◽  
pp. 7035-7048 ◽  
Author(s):  
Xianqiang Kong ◽  
Huizi Zhang ◽  
Yunqing Xiao ◽  
Changsheng Cao ◽  
Yanhui Shi ◽  
...  
Keyword(s):  
Transition Metal ◽  
Aromatic Amines ◽  
Bond Cleavage ◽  
Metal Free ◽  
Mild Conditions

A simple and effective aromatic nucleophilic monosubstitution reaction for the synthesis of aromatic amines via selective C–F bond cleavage of various fluoroarenes with primary and secondary aromatic amines is demonstrated.

Formal nucleophilic borylation and borylative cyclization of organic halides

2017 ◽  
Vol 15 (2) ◽  
pp. 285-300 ◽  
Author(s):  
K. Kubota ◽  
H. Iwamoto ◽  
H. Ito
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Recent Advances ◽  
Organic Halides ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Recent advances in borylations of organic halides, including both transition-metal-catalyzed and metal-free methods are summarized. Borylative cyclization is also discussed.

Catalytic Deoxygenative Cyclopropanation of 1,2-Dicarbonyl or Monocarbonyl Compounds via Molybdenum Catalysis

Synlett ◽  
2021 ◽  
Author(s):  
Jia-Le Wang ◽  
Chun-Xiang Zhuo
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Diazo Compounds ◽  
Recent Advances ◽  
Metal Carbenes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The cyclopropanation of alkenes through the transition-metal-catalyzed decomposition of diazo compounds is a powerful and straightforward strategy to produce cyclopropanes. Nevertheless, the appeal of further application of this strategy is tempered by the potentially explosive nature of the diazo substrates. Therefore, it is highly desirable to develop sustainable and operationally safe surrogates for diazo compounds. In this synpacts article, we discuss recent advances on the cyclopropane syntheses through the catalytic cyclopropanation of alkenes and metal-carbenes generated in-situ from non-diazo precursors, as well as highlight our recent progress on the unprecedented molybdenum-catalyzed deoxygenative cyclopropanation reaction of 1,2-dicarbonyl or monocarbonyl compounds.

Transition metal-free C-3 functionalization of quinoxalin-2(1H)-ones: recent advances and sanguine future

2021 ◽  
Author(s):  
Kiran ◽  
Payal Rani ◽  
Sandhya Chahal ◽  
Jayant Sindhu ◽  
Sudhir Kumar ◽  
...  
Keyword(s):  
Transition Metal ◽  
Environmentally Benign ◽  
Metal Free ◽  
Gradual Shift ◽  
Recent Advances ◽  
Metal Catalyzed

A gradual shift from metal-catalyzed to metal-free methods is occurring, as the latter are more environmentally benign. This review discusses sustainable protocols for the construction of C–C, C–N, C–P, C–S, and C–O bonds via C–H functionalization of quinoxalin-2(1H)-ones.

Recent advances in transition-metal-catalyzed reactions of alkynes with isoxazoles

2017 ◽  
Vol 15 (40) ◽  
pp. 8483-8492 ◽  
Author(s):  
Long Li ◽  
Tong-De Tan ◽  
Ying-Qi Zhang ◽  
Xin Liu ◽  
Long-Wu Ye
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Efficient Synthesis ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

In this review, recent progress in the transition-metal-catalyzed formal annulations of alkynes with isoxazoles for the efficient synthesis of N-heterocycles is discussed.

Recent Advances in Direct C–H Functionalization of Pyrimidines

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 193-210 ◽  
Author(s):  
Egor Verbitskiy ◽  
Gennady Rusinov ◽  
Oleg Chupakhin ◽  
Valery Charushin
Keyword(s):  
Transition Metal ◽  
Pyrimidine Derivatives ◽  
Metal Free ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions

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