Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides

2017 ◽  
Vol 15 (45) ◽  
pp. 9638-9642 ◽  
Author(s):  
Yaqi Yang ◽  
Zihang Ye ◽  
Xu Zhang ◽  
Yipeng Zhou ◽  
Xiantao Ma ◽  
...  
Keyword(s):  
Transition Metal ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Alkylation Reaction

Alcohols can be efficiently converted into thioethers by a transition metal- and base-free alkyl halide-catalyzed S-alkylation reaction with thiols or disulfides.

Unactivated Alkyl Halides in Transition-Metal-Catalyzed C–H Bond Alkylation

ACS Catalysis ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 3268-3292
Author(s):  
Shidheshwar B. Ankade ◽  
Anand B. Shabade ◽  
Vineeta Soni ◽  
Benudhar Punji
Keyword(s):  
Transition Metal ◽  
Alkyl Halides ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

scholarly journals Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1258-1267 ◽  
Author(s):  
Hajime Ito ◽  
Eiji Yamamoto ◽  
Satoshi Maeda ◽  
Tetsuya Taketsugu
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Experimental Studies ◽  
Transition Metal Catalysts ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Nucleophilic Attack ◽  
Important Class ◽  
Mechanistic Studies ◽  
Induced Reaction

Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si–B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This boryl­ation reaction is further applied to the first direct dimesitylboryl (BMes2) substitution of aryl halides using Ph2MeSi–BMes2 and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials.1 Introduction2 Boryl Substitution of Organohalides with PhMe2Si–B(pin)/Alkoxy Bases3 Mechanistic Investigations4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi–BMes2/Na(O-t-Bu)6 Conclusion

ChemInform Abstract: Indium-Copper and Indium-Silver Mediated Barbier-Grignard-Type Alkylation Reaction of Aldehydes Using Unactivated Alkyl Halides in Water

ChemInform ◽  
2008 ◽  
Vol 39 (38) ◽  
Author(s):  
Zhi-Liang Shen ◽  
Yan-Lin Yeo ◽  
Teck-Peng Loh
Keyword(s):  
Alkyl Halides ◽  
Alkylation Reaction

scholarly journals Pd-Catalyzed Cross-Electrophile Coupling/C–H Alkylation Reaction Enabled by a Mediator Generated via C(sp3)–H Activation

2021 ◽  
Author(s):  
Zhuo Wu ◽  
Hang Jiang ◽  
Yanghui Zhang
Keyword(s):  
Transition Metal ◽  
Alkyl Group ◽  
Alkylation Reaction ◽  
Aromatic Rings ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Alkylation Reactions

Transition-metal-catalyzed cross-electrophile C(sp2)–(sp3) coupling and C–H alkylation reactions represent two efficient methods for the incorpration of an alkyl group into aromatic rings. Herein, we report a Pd-catalyzed cascade cross-electrophile coupling...

ChemInform Abstract: Anomalous Reactivity of Silylborane: Transition-Metal-Free Boryl Substitution of Aryl, Alkenyl, and Alkyl Halides with Silylborane/Alkoxy Base Systems.

ChemInform ◽  
2013 ◽  
Vol 44 (20) ◽  
pp. no-no
Author(s):  
Eiji Yamamoto ◽  
Kiyotaka Izumi ◽  
Yuko Horita ◽  
Hajime Ito
Keyword(s):  
Transition Metal ◽  
Alkyl Halides ◽  
Metal Free

scholarly journals Transition-Metal (Pd, Ni, Mn)-Catalyzed C–C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks

2019 ◽  
Vol 52 (4) ◽  
pp. 1134-1144 ◽  
Author(s):  
Megan R. Kwiatkowski ◽  
Erik J. Alexanian
Keyword(s):  
Transition Metal ◽  
Building Blocks ◽  
Alkyl Halides

Binding of alkyl halides in water-soluble cavitands with urea rims

2018 ◽  
Vol 42 (12) ◽  
pp. 9945-9948 ◽  
Author(s):  
Yang Yu ◽  
Yong-Sheng Li ◽  
Julius Rebek
Keyword(s):  
Alkyl Halide ◽  
Alkyl Halides ◽  
Water Soluble

Alkyl halide guests in cavitands move rapidly and maintain halide to contact with the aryl surfaces of the host.

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.

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