Rh(iii)- or Ir(iii)-catalyzed ynone synthesis from aldehydes via chelation-assisted C–H bond activation

2015 ◽  
Vol 51 (37) ◽  
pp. 7871-7874 ◽  
Author(s):  
Wen Ai ◽  
Yunxiang Wu ◽  
Huanyu Tang ◽  
Xueyan Yang ◽  
Yaxi Yang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Reaction Conditions ◽  
Practical Synthesis ◽  
First Time

A simple and practical synthesis of ynones directly from readily available aldehydes was developed for the first time under mild reaction conditions via a Rh(iii)- or Ir(iii)-catalyzed formyl C–H bond activation.

scholarly journals A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 107-117
Author(s):  
Mattia Forchetta ◽  
Valeria Conte ◽  
Giulia Fiorani ◽  
Pierluca Galloni ◽  
Federica Sabuzi
Keyword(s):  
Metal Oxides ◽  
Phosphonic Acid ◽  
Organic Molecules ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Phosphonic Acids ◽  
Sustainable Improvement ◽  
Phosphonate Esters ◽  
First Time ◽  
Complex Organic

Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

Sulfonyl Radical Triggered Selective Iodosulfonylation and Bicycli-zations of 1,6-Dienes

2021 ◽  
Author(s):  
Shi-Ping Wu ◽  
Dong-Kai Wang ◽  
Qing-Qing Kang ◽  
Guo-Ping Ge ◽  
Hongxing Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Selectivity ◽  
Reaction Conditions ◽  
First Time

A novel sulfonyl radical triggered selective iodosulfonylation and bicyclizations of 1,6-dienes has been described for the first time. High selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and...

TBAI Catalyzed Electrochemical C-H Bond Activation of 2-arylated-N-methoxyamides for the Synthesis of Phenanthridinones

Synlett ◽  
2021 ◽  
Author(s):  
Kripa Subramanian ◽  
Subhash L. Yedage ◽  
Kashish Sethi ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Electrochemical Method ◽  
Bond Activation ◽  
Supporting Electrolyte ◽  
Bioactive Compound ◽  
Reaction Conditions ◽  
Redox Catalyst ◽  
Synthetic Utility ◽  
One Step ◽  
Constant Potential

An electrochemical method for the synthesis of phenanthridinones via constant potential electrolysis (CPE) mediated by <i>n</i>-Bu<sub>4</sub>NI (TBAI) has been reported. The protocol is metal and oxidant free and proceeds with 100% current efficiency. Here TBAI plays the dual role of the redox catalyst as well as supporting electrolyte. The intramolecular C-H activation proceeds under mild reaction conditions and short reaction time via electrochemically generated amidyl radicals. The reaction has been scaled up to gram level showing its practicability and the synthetic utility and applicability of the protocol has been demonstrated by the direct one-step synthesis of the bioactive compound Phenaglaydon.

scholarly journals Cross‐Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel‐Catalyzed CO Bond Activation under Mild Reaction Conditions

2009 ◽  
Vol 48 (8) ◽  
pp. 1351-1351
Author(s):  
Bi‐Jie Li ◽  
Yi‐Zhou Li ◽  
Xing‐Yu Lu ◽  
Jia Liu ◽  
Bing‐Tao Guan ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Organozinc Reagents

scholarly journals New opportunities in the stereoselective dearomatization of indoles

2016 ◽  
Vol 88 (3) ◽  
pp. 207-214 ◽  
Author(s):  
Elisabetta Manoni ◽  
Assunta De Nisi ◽  
Marco Bandini
Keyword(s):  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
High Yields ◽  
First Time ◽  
Tailored Design ◽  
Bronsted Acid Catalysis

AbstractThe regio- and stereoselective dearomatization of indoles is realized for the first time by combining readily available indolyl precursors and electron-rich allenes, namely allenamides and aryloxyallenes. Inter- as well as intramolecular condensations were realized under gold and Brønsted acid catalysis providing a range of densely functionalized indoline and indolenine cores in high yields and excellent stereochemical outcome. Chemodivergent reaction profiles (Micheal-type addition vs. [2+2]-cycloaddition) were realized by a tailored design of both reaction conditions and functionalization of the reaction partners.

scholarly journals SYNTHESIS OF AN AZIDE–THIOL LINKER FOR HETEROGENEOUS POLYMER FUNCTIONALIZATION VIA THE “CLICK” REACTION

2018 ◽  
Vol 55 (1B) ◽  
pp. 152
Author(s):  
Thuy Thu Truong
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Click Reaction ◽  
Proton Nuclear Magnetic Resonance ◽  
Reaction Yield ◽  
Reaction Conditions ◽  
Click Reactions ◽  
Heterogeneous Polymer ◽  
Ft Ir ◽  
First Time ◽  
Layer Chromatography

In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). The employment of the obtained azide–thiol linker in heterogeneous polymer “click” functionalization was demonstrated for the first time, which was monitored by an online FT–IR method. The obtained telechelic azide–thiol linker is envisioned to be useful chemical tools to link macromolecular chains via orthogonal click reactions.

scholarly journals Efficient N-formylation of primary aromatic amines using novel solid acid magnetic nanocatalyst

RSC Advances ◽  
2020 ◽  
Vol 10 (67) ◽  
pp. 41229-41236
Author(s):  
Jitendra Kumar Yadav ◽  
Priyanka Yadav ◽  
Satish K. Awasthi ◽  
Alka Agarwal
Keyword(s):  
Magnetic Nanoparticles ◽  
Aromatic Amines ◽  
Sulfonic Acid ◽  
Solid Acid ◽  
Recyclable Catalyst ◽  
Primary Amines ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
First Time

Sulfonic acid functionalized over biguanidine fabricated silica-coated heterogeneous magnetic nanoparticles (NP@SO3H) have been synthesized, well characterized and explored for the first time, as an efficient and recyclable catalyst for N-formylation of primary amines under mild reaction conditions.

Deep eutectic solvent-catalyzed Meyer–Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

2020 ◽  
Vol 56 (96) ◽  
pp. 15165-15168
Author(s):  
Nicolás Ríos-Lombardía ◽  
Luciana Cicco ◽  
Kota Yamamoto ◽  
José A. Hernández-Fernández ◽  
Francisco Morís ◽  
...  
Keyword(s):  
Room Temperature ◽  
Deep Eutectic Solvent ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
First Time

Faster, milder, greener…better! The Meyer–Schuster rearrangement is disclosed for the first time in a deep eutectic solvent, namely FeCl3·6H2O/glycerol (3 : 1), enabling the reaction at room temperature, under air and with short reaction times.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

2020 ◽  
Vol 44 (5-6) ◽  
pp. 301-304
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Ruoqi Yang ◽  
Fengzhe Guo ◽  
Zi-Long Tang ◽  
...  
Keyword(s):  
Aromatic Acid ◽  
Aliphatic Acid ◽  
Acid Chlorides ◽  
Alkyl Esters ◽  
Reaction Conditions ◽  
Simple Reaction ◽  
Tert Butyl ◽  
Butyl Esters ◽  
Plausible Mechanism ◽  
First Time

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

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