Recent advances in the sulfonylation of C–H bonds with the insertion of sulfur dioxide

2018 ◽  
Vol 54 (89) ◽  
pp. 12561-12569 ◽  
Author(s):  
Guanyinsheng Qiu ◽  
Kaida Zhou ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Metal Catalysis ◽  
Radical Process ◽  
Recent Advances

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.

scholarly journals TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 355 ◽  
Author(s):  
Yi Wang ◽  
Anan Liu ◽  
Dongge Ma ◽  
Shuhong Li ◽  
Chichong Lu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Tio2 Photocatalysis ◽  
Mild Conditions

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.

Fixation of sulfur dioxide into small molecules

2015 ◽  
Vol 13 (6) ◽  
pp. 1592-1599 ◽  
Author(s):  
Gang Liu ◽  
Congbin Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Small Molecules ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Radical Process ◽  
Metal Free ◽  
Recent Advances

Recent advances in the insertion of sulfur dioxide under transition metal catalysis or metal-free conditions via a radical process are presented.

Recent advances in sulfonylation reactions using potassium/sodium metabisulfite

2020 ◽  
Vol 56 (30) ◽  
pp. 4145-4155 ◽  
Author(s):  
Shengqing Ye ◽  
Min Yang ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Sodium Metabisulfite ◽  
Metal Catalysis ◽  
Potassium Sodium ◽  
Mild Conditions ◽  
Recent Advances ◽  
Radical Processes

Recently, sulfonylation reactions using potassium/sodium metabisulfite as the sulfur dioxide surrogate have been developed rapidly. In most cases, the transformations go through radical processes with the insertion of sulfur dioxide under mild conditions. Additionally, transition metal catalysis is applied in the reactions for the synthesis of sulfonyl-containing compounds.

Visible Light-Induced Transition Metal Catalysis

2021 ◽  
Author(s):  
Kelvin Pak Shing Cheung ◽  
Sumon Sarkar ◽  
Vladimir Gevorgyan
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide

2020 ◽  
Vol 22 (6) ◽  
pp. 1906-1910 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Xiaona Fan ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

2017 ◽  
Vol 4 (9) ◽  
pp. 1745-1750 ◽  
Author(s):  
Yuewen Li ◽  
Yiye Lu ◽  
Runyu Mao ◽  
Zhiming Li ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Halogen Bond ◽  
Theoretical Calculations ◽  
Light Irradiation ◽  
Efficient Catalyst ◽  
Photoinduced Reaction ◽  
Plausible Mechanism ◽  
Perfluoroalkyl Halides

The sulfur dioxide surrogate of DABCO·(SO2)2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation. A plausible mechanism supported by theoretical calculations is proposed.

Photocatalyst- and transition-metal-free α-allylation of N-aryl tetrahydroisoquinolines mediated by visible light

2020 ◽  
Vol 22 (3) ◽  
pp. 646-650 ◽  
Author(s):  
Zhuohua Li ◽  
Pengju Ma ◽  
Yongzhu Tan ◽  
Yufei Liu ◽  
Min Gao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Metal Free

A convenient and efficient α-allylation of N-aryl tetrahydroisoquinolines has been achieved. This transformation can be realized under only visible light irradiation without the aid of transition metals or photocatalysts.

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
Keyword(s):  
Transition Metal ◽  
Photochemical Reactions ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Diazo Compounds ◽  
Metal Catalysis ◽  
Recent Developments

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.

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