Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols

2018 ◽  
Vol 90 (2) ◽  
pp. 377-386 ◽  
Author(s):  
Klara Čebular ◽  
Stojan Stavber

Abstract C–C bond formation is one of the most fundamental approaches toward molecular diversity in organic synthesis. In pursuit of environmentally friendlier chemical approaches to organic chemistry, we present a new metal-free method for direct dehydrative cross-coupling of alcohols and alkenes using molecular iodine as a Lewis acid catalyst under solvent-free reaction conditions. The reaction is atom-economical, tolerant to air and allows simple synthetic procedure, furnishing Csp3–Csp2 coupling products with yields up to 97%. The method has proved efficient for coupling of secondary benzyl alcohols with phenyl-substituted alkenes.

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 850
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber

C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.


2019 ◽  
Author(s):  
Robert Harris ◽  
Jiyong Park ◽  
Taylor Nelson ◽  
Nafees Iqbal ◽  
Daniel Salgueiro ◽  
...  

The mechanism of catalytic allylic C–H amination reactions promoted by Cp*Rh complexes is reported. Reaction kinetics experiments, stoichiometric studies, and DFT calculations demonstrate that allylic C–H activation to generate a Cp*Rh(π-allyl) complex is viable under mild reaction conditions. The role of external oxidant in the catalytic cycle is elucidated. Quantum mechanical calculations, stoichiometric reactions, and cyclic voltammetry<b></b>experiments support an oxidatively induced reductive elimination process of the allyl fragment with an acetate ligand. Lastly, evidences supporting the amination of an allylic acetate intermediate is presented. Both nucleophilic substitution catalyzed by Ag<sup>+</sup>that behaves as a Lewis acid catalyst and an inner-sphere amination catalyzed by Cp*Rh are shown to be viable for the last step of the allylic amination reaction.


Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 235-237
Author(s):  
Amarsinha Gorepatil ◽  
Pratapsinha Gorepatil ◽  
Mahadev Gaikwad ◽  
Dattakumar Mhamane ◽  
Ajit Phadkule ◽  
...  

A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o-aminochalcones with zirconyl nitrate [Zn(O)(NO3)2·nH2O] as a water-tolerant Lewis-acid catalyst.


2009 ◽  
Vol 2009 (10) ◽  
pp. 638-641 ◽  
Author(s):  
Xufeng Lin ◽  
Jun Wang ◽  
Fangxi Xu ◽  
Yanguang Wang

A highly efficient method for the C–N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allylic amides in moderate to excellent yields. The significan features of the procedure include mild and metal-free reaction conditions, operational simplicity, inexpensive reagents, short reaction time, and good yields.


2015 ◽  
Vol 51 (35) ◽  
pp. 7540-7542 ◽  
Author(s):  
Ji-Shu Zhang ◽  
Tieqiao Chen ◽  
Jia Yang ◽  
Li-Biao Han

Nickel-catalysed P–H/C–CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp2C–P bonds. This transformation provides a convenient method for the preparation of both arylphosphines and arylphosphine oxides from the readily available P–H compounds and arylnitriles.


2009 ◽  
Vol 66 (9) ◽  
pp. 341-348
Author(s):  
Pei YAN ◽  
Tomohisa TEMMA ◽  
Hideyuki TAGAYA ◽  
Shigeki HABAUE

ChemInform ◽  
2003 ◽  
Vol 34 (46) ◽  
Author(s):  
Pentlavalli Sreekanth ◽  
Sang-Wook Kim ◽  
Taegwhan Hyeon ◽  
B. Moon Kim

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