Titanium Alkoxide-Based Regioselective Alkyne–Alkyne Reductive Coupling Mediated by In Situ Generated Arylamidate

2020 ◽  
Vol 142 (8) ◽  
pp. 3729-3735
Author(s):  
Bin Cai ◽  
James S. Panek
Keyword(s):  
Reductive Coupling ◽  
Titanium Alkoxide

Carbon–Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Grignard Reagent ◽  
Iron Catalyst ◽  
Alkyl Halide ◽  
Titanocene Dichloride ◽  
Secondary Amide ◽  
Reductive Coupling ◽  
Quaternary Centers ◽  
Carbon Carbon Bond ◽  
The University

Daniel J. Weix of the University of Rochester effected (Org. Lett. 2012, 14, 1476) the in situ reductive coupling of an alkyl halide 2 with an acid chloride 1 to deliver the ketone 3. André B. Charette of the Université de Montréal (not illustrated) developed (Nature Chem. 2012, 4, 228) an alternative route to ketones by the coupling of an organometallic with an in situ-activated secondary amide. Mahbub Alam and Christopher Wise of the Merck, Sharpe and Dohme UK chemical process group optimized (Org. Process Res. Dev. 2012, 16, 453) the opening of an epoxide 4 with a Grignard reagent 5. Ling Song of the Fujian Institute of Research on the Structure of Matter optimized (J. Org. Chem. 2012, 77, 4645) conditions for the 1,2-addition of a Grignard reagent (not illustrated) to a readily enolizable ketone. Wei-Wei Liao of Jilin University conceived (Org. Lett. 2012, 14, 2354) of an elegant assembly of highly functionalized quaternary centers, as illustrated by the conversion of 7 to 8. Antonio Rosales of the University of Granada and Ignacio Rodríguez-García of the University of Almería prepared (J. Org. Chem. 2012, 77, 4171) free radicals by reduction of an ozonide 9 in the presence of catalytic titanocene dichloride. In the absence of the acceptor 10, the dimer of the radical was obtained, presenting a simple alternative to the classic Kolbe coupling. Marc L. Snapper of Boston College found (Eur. J. Org. Chem. 2012, 2308) that the difficult ketone 12 could be methylenated following a modified Peterson protocol. Yoshito Kishi of Harvard University optimized (Org. Lett. 2012, 14, 86) the coupling of 15 with 16 to give 17. Masaharu Nakamura of Kyoto University devised (J. Org. Chem. 2012, 77, 1168) an iron catalyst for the coupling of 18 with 19. The specific preparation of trisubsituted alkenes is an ongoing challenge. Quanri Wang of Fudan University and Andreas Goeke of Givaudan Shanghai fragmented (Angew. Chem. Int. Ed. 2012, 51, 5647) the ketone 21 by exposure to 22 to give the macrolide 23 with high stereocontrol.

Hybrid polymer/TiO2 films by in situ hydrolysis condensation of titanium alkoxide precursors for photovoltaic transparent windows

2010 ◽  
Vol 207 (7) ◽  
pp. 1627-1630 ◽  
Author(s):  
Joël Davenas ◽  
Vincent Barlier ◽  
Véronique-Bounor Legaré ◽  
Bruno Canut ◽  
Andrzej Rybak ◽  
...  
Keyword(s):  
Tio2 Films ◽  
Titanium Alkoxide ◽  
Hybrid Polymer ◽  
Transparent Windows ◽  
Alkoxide Precursors

Synthesis of fluorinated gradient copolymers via in situ transesterification with fluoroalcohols in tandem living radical polymerization

2017 ◽  
Vol 8 (15) ◽  
pp. 2299-2308 ◽  
Author(s):  
Yusuke Ogura ◽  
Takaya Terashima ◽  
Mitsuo Sawamoto
Keyword(s):  
Methyl Methacrylate ◽  
Radical Polymerization ◽  
Living Radical Polymerization ◽  
Titanium Alkoxide ◽  
Tandem Catalysis ◽  
In Situ Transesterification ◽  
Gradient Copolymers

Fluorinated gradient copolymers were synthesized by the tandem catalysis of ruthenium-catalyzed living radical polymerization and titanium alkoxide-mediated transesterification of methyl methacrylate (MMA) with fluoroalcohols.

Oxalate Bridged Copper Pyrazole Complex Templated Anderson-Evans Cluster Based Solids

2011 ◽  
Vol 64 (1) ◽  
pp. 68 ◽  
Author(s):  
Katikaneani Pavani ◽  
Monika Singh ◽  
Arunachalam Ramanan
Keyword(s):  
Room Temperature ◽  
Reaction Medium ◽  
Sodium Molybdate ◽  
Supramolecular Interactions ◽  
Reductive Coupling ◽  
Dissolved Carbon ◽  
Dissolved Carbon Dioxide ◽  
1D Chain ◽  
Covalently Linked

The synthesis of four new Anderson-Evans type cluster based solids was carried out from an aqueous solution containing sodium molybdate, chromium chloride, cupric chloride and pyrazole at room temperature: [{Cr3O(CH3COO)6(H2O)3}2{H7CrMo6O24}]·24H2O, 1; [{Cu2(ox)(pz)4}{H7CrMo6O24}]·11H2O, 3; [{Cu(pz)2(H2O)2}{Cu2(ox)(pz)4}{H5CrMo6O24}]·8H2O, 4; and [{Cu(pz)3Cl}{Cu2(ox)(pz)4}{H6CrMo6O24}]·8H2O, 5. In 1, the discrete Anderson-Evans cluster aggregates with trimeric chromium acetate cationic complex through supramolecular interactions. In 3–5, the Anderson-Evans cluster is covalently linked into a 1D chain through oxalate bridged copper pyrazole units. In 3, the chains are further stabilized by water oligomers. In 4 and 5, the chains are covalently linked into 2D sheets by different copper pyrazole complexes. The oxalate molecules in 3–5 are probably generated in situ in the reaction medium, through a reductive coupling of dissolved carbon dioxide assisted by copper pyrazole units.

Bismuth nanoparticles: an efficient catalyst for reductive coupling of nitroarenes to azo-compounds

RSC Advances ◽  
2015 ◽  
Vol 5 (101) ◽  
pp. 83144-83148 ◽  
Author(s):  
Kishore Pothula ◽  
Lin Tang ◽  
Zhenggen Zha ◽  
Zhiyong Wang
Keyword(s):  
Azo Compounds ◽  
Reductive Coupling ◽  
Efficient Catalyst ◽  
Bismuth Nanoparticles

The synthesis of azoarenes from corresponding nitroarenes was developed by virtue of in situ bismuth nanoparticles.

scholarly journals Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical

2018 ◽  
Vol 9 (15) ◽  
pp. 3664-3671 ◽  
Author(s):  
Jia Cao ◽  
Guoqiang Wang ◽  
Liuzhou Gao ◽  
Xu Cheng ◽  
Shuhua Li
Keyword(s):  
Coupling Reaction ◽  
Reductive Coupling

A pyridine-boryl radical promoted reductive coupling reaction of aldehydes with 1,1-diarylethylenes has been established.

A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ

RSC Advances ◽  
2015 ◽  
Vol 5 (78) ◽  
pp. 63726-63731 ◽  
Author(s):  
Xu Shen ◽  
Ningning Gu ◽  
Ping Liu ◽  
Xiaowei Ma ◽  
Jianwei Xie ◽  
...  
Keyword(s):  
Synthesis Method ◽  
Reductive Coupling ◽  
Efficient Synthesis ◽  
Metal Free ◽  
Arylboronic Acids

A general, yet efficient synthesis method of 9-arylfluorenes via metal-free reductive coupling of N-tosylhydrazones and arylboronic acids has been developed.

scholarly journals Confronting the Challenging Asymmetric Addition of Vinyl Arene Pronucleophiles into Ketones: Ligand-Controlled Regiodivergent Processes Through a Dearomatized Allyl-Cu Species

2021 ◽  
Author(s):  
Yuyang Dong ◽  
Alexander Schuppe ◽  
Binh Khanh Mai ◽  
Peng Liu ◽  
Stephen Buchwald
Keyword(s):  
Transition State ◽  
Functional Groups ◽  
Computational Studies ◽  
Ancillary Ligand ◽  
Reductive Coupling ◽  
Cyclic Transition ◽  
Tertiary Alcohols ◽  
Rapid Construction ◽  
Cyclic Transition State

The selective reductive coupling of vinyl arenes and ketones represents a versatile approach for the rapid construction of enantiomerically enriched tertiary alcohols. Herein, we demonstrate a CuH-catalyzed regiodivergent coupling of vinyl arenes and ketones, in which the selectivity is controlled by the ancillary ligand. This approach leverages an in situ generated benzyl- or dearomatized allyl-Cu intermediate, yielding either the dearomatized or exocyclic addition products, respectively. The method exhibits excellent regio-, diastereo- and enantioselectivity, and tolerates a range of common functional groups and heterocycles. Computational studies suggest that the regio- and enantioselectivity are controlled by the ancillary ligand, while the diastereoselectivity is enforced by steric interactions between the alkyl-Cu intermediate and ketone substrates in a six-membered cyclic transition state.

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