Merging Transition-Metal Catalysis with Photoredox Catalysis: An Environmentally Friendly Strategy for C–H Functionalization

Synthesis ◽  
2018 ◽  
Vol 50 (17) ◽  
pp. 3359-3378 ◽  
Author(s):  
Wen-Jun Zhou ◽  
Da-Gang Yu ◽  
Yi-Han Zhang ◽  
Yong-Yuan Gui ◽  
Liang Sun
Keyword(s):  
Transition Metal ◽  
High Selectivity ◽  
Rapid Development ◽  
Palladium Catalysis ◽  
Transition Metal Catalysis ◽  
Nickel Catalysis ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Metal Catalysis ◽  
Metal Catalyzed

Transition-metal-catalyzed C–H functionalization is already a useful tool in organic synthesis, whilst the rapid development of photoredox catalysis provides new pathways for C–H functionalization with high selectivity and efficiency under mild reaction conditions. In this review, recent advances in C–H functionalization through merging transition­-metal catalysis with photoredox catalysis are discussed.1 Introduction2 Merging Nickel Catalysis with Photoredox Catalysis3 Merging Palladium Catalysis with Photoredox Catalysis4 Merging Cobalt Catalysis with Photoredox Catalysis5 Merging Photoredox Catalysis with Other Transition-Metal Catalysis­6 Conclusions

scholarly journals The A3 Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines: A Comparative Study between Visible Light Photocatalysis and Transition-Metal Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Vladimir V. Kouznetsov ◽  
Marlyn C. Ortiz Villamizar ◽  
Carlos E. Puerto Galvis
Keyword(s):  
Transition Metal ◽  
Microwave Irradiation ◽  
Visible Light ◽  
High Selectivity ◽  
Transition Metal Catalysis ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions ◽  
Metal Catalysis ◽  
New Compounds ◽  
Optimal Reaction

AbstractConsidering the current challenges of the A3 redox-neutral C1-alkynylation of tetrahydroisoquinolines (THIQs), we studied this synthetic tool under visible light photocatalysis and transition-metal catalysis in order to describe alternative reaction conditions and discuss possible improvements to this process. We demonstrated that 1-alkynylated THIQs can be readily obtained by three different approaches: iridium-based photocatalysis and copper ([CuBr(PPh3)3]) and silver (AgNO3) catalysis under mild, selective and accessible reaction conditions. Among these approaches, the copper(I)-based methodology resulted in the most robust, optimal reaction conditions for the synthesis of a series of 18 1-alkynylated THIQs in moderate to excellent yields and with high selectivity for the endo-alkynylated products. Moreover, this reaction can be accelerated by microwave irradiation (120 °C, 15 min) affording a novel library of diverse THIQs with alkyne and N-substituent moieties, from unreactive and uncommon substrates, that could be further transformed into new compounds of interest.

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

2017 ◽  
Vol 4 (10) ◽  
pp. 1981-1986 ◽  
Author(s):  
Huijie Qiao ◽  
Suyan Sun ◽  
Yue Zhang ◽  
Hongmei Zhu ◽  
Xiaomeng Yu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

A simple and efficient protocol for the transition metal-catalyzed site-selective C–H phosphonation of 8-aminoquinoline at the C4 or C5 positions via a photoredox process was developed.

The C–H functionalization of N-alkoxycarbamoyl indoles by transition metal catalysis

2021 ◽  
Vol 19 (37) ◽  
pp. 7949-7969
Author(s):  
Prasanjit Ghosh ◽  
Sajal Das
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Indole and its congeners are ubiquitous nitrogen containing organic scaffolds found in a plethora of natural products. This review aims to highlight the transition-metal catalyzed C–H functionalization of N-alkoxycarbamoyl indoles.

scholarly journals Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 612-628 ◽  
Author(s):  
Janakiram Vaitla ◽  
Annette Bayer
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Transition Metal Catalysis ◽  
Transfer Reactions ◽  
Reaction Conditions ◽  
Widespread Application ◽  
Metal Catalysis ◽  
Half Century ◽  
Metal Carbenoids

As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.1 Introduction2 Preparation of Sulfoxonium Ylides3 Investigation for Carbenoid Formation from Sulfoxonium Ylide 4 X–H (X = N, O, S, C) Functionalization Reactions5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides6 Conclusion and Perspective

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.

Recent development of synthetic preparation methods for guanidines via transition metal catalysis

2015 ◽  
Vol 51 (2) ◽  
pp. 254-265 ◽  
Author(s):  
Wen-Xiong Zhang ◽  
Ling Xu ◽  
Zhenfeng Xi
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Preparation Methods ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

This article provides an overview of guanidine synthesis via transition-metal-catalyzed reactions including cycloaddition, guanylation and tandem guanylation/cyclization.

scholarly journals Recent Developments in Transition-Metal Catalyzed Direct C–H Alkenylation, Alkylation, and Alkynylation of Azoles

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4970
Author(s):  
Su Chen ◽  
Prabhat Ranjan ◽  
Leonid G. Voskressensky ◽  
Erik V. Van der Eycken ◽  
Upendra K. Sharma
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Significant Progress ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Regioselective Alkylation ◽  
Recent Developments ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

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.

Transition metal-catalyzed direct nucleophilic addition of C–H bonds to carbon–heteroatom double bonds

2014 ◽  
Vol 5 (6) ◽  
pp. 2146-2159 ◽  
Author(s):  
Xi-Sha Zhang ◽  
Kang Chen ◽  
Zhang-Jie Shi
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Transition Metal Catalysis ◽  
Grignard Reaction ◽  
Double Bonds ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Compared with the traditional Grignard reaction, direct insertion of polar double bonds to C–H bonds via transition-metal catalysis is ideal from the viewpoint of atom-, step- and cost-economy and the avoidance of the waste emission, as well as of the complex manipulation of sensitive reagents.

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