Recent Advances on Catalytic Enantioselective Direct C-H Bond Functionalization of Electron-Deficient N-Containing Heteroarenes

Author(s):  
Xiao-Lan Liu ◽  
Luo-Bin Jiang ◽  
Mupeng Luo ◽  
Zhi Ren ◽  
Shou-Guo Wang

Catalytic enantioselective direct C-H bond functionalization of electron-deficient N-containing heteroarenes represents one of the most straightforward and powerful protocols to construct diverse enantioenriched highly functionalized N-heteroarene products. Efficient catalytic systems...

2021 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Aishwarya K. Dalvi ◽  
Adithyaraj Koodan ◽  
Siddhartha Maiti ◽  
Shaeel Al-Thabaiti ◽  
...  

Carbon dioxide (CO2) has emerged as one of the exciting cost-effective, abundant, and ready-to-use C1 sources in synthetic organic chemistry. However, the thermodynamic stability, as well as the kinetic inertness,...


Author(s):  
Marco Antônio G. B. Gomes ◽  
Christiane Fernandes ◽  
Lawrence R. Gahan ◽  
Gerhard Schenk ◽  
Adolfo Horn

2020 ◽  
Vol 16 ◽  
pp. 212-232 ◽  
Author(s):  
Delphine Pichon ◽  
Jennifer Morvan ◽  
Christophe Crévisy ◽  
Marc Mauduit

The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, N-acyloxazolidinones, N-acylpyrrolidinones, amides, N-acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.


2017 ◽  
Vol 37 (7) ◽  
pp. 1613 ◽  
Author(s):  
Longzhi Zhu ◽  
Xin Cao ◽  
You Li ◽  
Ting Liu ◽  
Xie Wang ◽  
...  

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4970
Author(s):  
Su Chen ◽  
Prabhat Ranjan ◽  
Leonid G. Voskressensky ◽  
Erik V. Van der Eycken ◽  
Upendra K. Sharma

The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous transformations in many cases. This review covers recent advances in the direct C–H alkenylation, alkylation and alkynylation of azoles utilizing transition metal-catalysis. Moreover, the limitations of different strategies, chemoselectivity and regioselectivity issues will be discussed in this review.


Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4367
Author(s):  
Quan-Qing Zhao ◽  
Xiao-Qiang Hu

Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.


2018 ◽  
Vol 47 (20) ◽  
pp. 7552-7576 ◽  
Author(s):  
Chunhui Shan ◽  
Lei Zhu ◽  
Ling-Bo Qu ◽  
Ruopeng Bai ◽  
Yu Lan

This review summarized recent advances in the mechanistic study of Ru-catalyzed C–H bond functionalization from a theoretical perspective.


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