Recent developments in photochemical reactions of diazo compounds

2019 ◽  
Vol 17 (3) ◽  
pp. 432-448 ◽  
Author(s):  
Łukasz W. Ciszewski ◽  
Katarzyna Rybicka-Jasińska ◽  
Dorota Gryko

Chemistry of diazo compounds is dominated by transition metal catalysis but recently, photoinitiated reactions of diazo compounds have attracted a lot of attention. This mini-review describes recent discoveries on the reactivity of diazo compounds under light irradiation.

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 355 ◽  
Author(s):  
Yi Wang ◽  
Anan Liu ◽  
Dongge Ma ◽  
Shuhong Li ◽  
Chichong Lu ◽  
...  

Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.


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.


2016 ◽  
Vol 14 (33) ◽  
pp. 7829-7831 ◽  
Author(s):  
Xiaojie Shang ◽  
Zhong-Quan Liu

As important and valuable alternatives to transition-metal-catalysis, free-radical strategies for C–Si bond construction via selective C–H/Si–H functionalization have been developed recently. These new reactions along with their suggested mechanisms are summarized and discussed here.


ACS Catalysis ◽  
2020 ◽  
Vol 10 (18) ◽  
pp. 10672-10714 ◽  
Author(s):  
Alexander Fanourakis ◽  
Philip J. Docherty ◽  
Padon Chuentragool ◽  
Robert J. Phipps

2016 ◽  
Vol 14 (34) ◽  
pp. 8014-8025 ◽  
Author(s):  
T. M. M. Maiden ◽  
J. P. A. Harrity

This review describes recent developments in the employment of catalytic methods for the synthesis of quinazolinones, an important class of heterocycles that are prevalent in a variety of important bio-active scaffolds.


2014 ◽  
Vol 12 (38) ◽  
pp. 7423-7432 ◽  
Author(s):  
Rachelle Quach ◽  
Daniel F. Chorley ◽  
Margaret A. Brimble

This perspective updates recent developments (since 2012) in the synthesis of spiroketals using transition metal catalysis.


2018 ◽  
Vol 54 (89) ◽  
pp. 12561-12569 ◽  
Author(s):  
Guanyinsheng Qiu ◽  
Kaida Zhou ◽  
Jie Wu

Recent advances in the sulfonylation of C–H bonds with the insertion of sulfur dioxide are summarized. C–H bond sulfonylation under transition metal catalysis or through a radical process has been developed. In some cases, the sulfonylation can be performed under catalyst- and additive-free conditions, or can be facilitated by visible light irradiation. The efficiency is also studied by merging the radical process and metal catalysis.


2021 ◽  
Author(s):  
Pratheepkumar Annamalai ◽  
Ke‐Chien Liu ◽  
Satpal Singh Badsara ◽  
Chin‐Fa Lee

Sign in / Sign up

Export Citation Format

Share Document