Synthesis of β-Keto SulfonesviaCoupling of Aryl/Alkyl Halides, Sulfur Dioxide and Silyl Enolates through Metal-Free Photoinduced C-X Bond Dissociation

2017 ◽  
Vol 359 (17) ◽  
pp. 2999-3004 ◽  
Author(s):  
Xinxing Gong ◽  
Yechun Ding ◽  
Xiaona Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Alkyl Halides ◽  
Metal Free ◽  
Bond Dissociation

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.

Transition‐Metal‐Free C2‐H Sulfonylation of Quinoline N ‐Oxides via Insertion of Sulfur Dioxide

2019 ◽  
Vol 8 (11) ◽  
pp. 2105-2108 ◽  
Author(s):  
Heng Cai ◽  
Huiyong Yang ◽  
Jun Xu ◽  
Hanyang Bao ◽  
Lin Huang ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Transition Metal ◽  
Metal Free

scholarly journals Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

2016 ◽  
Vol 12 ◽  
pp. 1153-1169 ◽  
Author(s):  
Nivesh Kumar ◽  
Santanu Ghosh ◽  
Subhajit Bhunia ◽  
Alakesh Bisai
Keyword(s):  
Transition Metal ◽  
Alkyl Halides ◽  
One Pot ◽  
Metal Free ◽  
Quaternary Center ◽  
Dehydrogenative Coupling ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

scholarly journals Electrochemically Driven Cross-Electrophile Coupling of Alkyl Halides

2021 ◽  
Author(s):  
Song Lin ◽  
Wen Zhang ◽  
Lingxiang Lu ◽  
Wendy Zhang ◽  
Jose Mondragon ◽  
...  
Keyword(s):  
High Selectivity ◽  
Alkyl Halide ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Critical Problem ◽  
Metal Free ◽  
Drug Candidates ◽  
Synthetic Accessibility ◽  
Alkyl Electrophiles ◽  
Direct Cross

Recent research in medicinal chemistry suggests a correlation between an increase in the fraction of sp3 carbons in drug candidates with their improved success rate in clinical trials. As such, the development of robust and selective methods for the construction of C(sp3)-C(sp3) bonds remains a critical problem in modern organic chemistry. Owing to the broad availability and synthetic accessibility of alkyl halides, their direct cross coupling—commonly known as cross-electrophile coupling (XEC)—provides a promising route toward this objective. However, achieving high selectivity in C(sp3)-C(sp3) XEC remains a largely unmet challenge. Herein, we employ electrochemistry to achieve the differential activation of alkyl halides by exploiting their disparate electronic and steric properties. Specifically, the selective cathodic reduction of a more substituted alkyl halide gives rise to a carbanion, which undergoes preferential coupling with a less substituted alkyl halide via bimolecular nucleophilic substitution (SN2) to forge a new C–C bond. This transition-metal free protocol enables the efficient XEC of a variety of functionalized and unactivated alkyl electrophiles and exhibits substantially improved chemoselectivity versus existing methodologies.

Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

2018 ◽  
Vol 13 (24) ◽  
pp. 3833-3837
Author(s):  
Ting Liu ◽  
Renhua Qiu ◽  
Longzhi Zhu ◽  
Shuang-Feng Yin ◽  
Chak-Tong Au ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Metal Free ◽  
Dialkyl Sulfides
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