An iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers

2015 ◽  
Vol 13 (24) ◽  
pp. 6737-6741 ◽  
Author(s):  
B. V. Subba Reddy ◽  
B. Someswarao ◽  
N. Prudhviraju ◽  
B. Jagan Mohan Reddy ◽  
B. Sridhar ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
High Selectivity ◽  
Molecular Iodine ◽  
Metal Free

A domino cyclization of 4-(2-hydroxyethyl)cyclohex-3-enol with aldehydes using 10 mol% molecular iodine is reported to produce oxygen bridged bicyclic ethers in good yields with high selectivity.

Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles

2017 ◽  
Vol 41 (1) ◽  
pp. 75-80 ◽  
Author(s):  
Sethurajan Ambethkar ◽  
Muthalu Vellimalai ◽  
Vediappen Padmini ◽  
Nattamai Bhuvanesh
Keyword(s):  
Reaction Time ◽  
Intramolecular Cyclization ◽  
Simple Procedure ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Regioselective Synthesis ◽  
Thiazole Derivatives ◽  
Short Reaction Time ◽  
Metal Free

The regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives via amination (C–N) and intramolecular cyclization (C–S) reactions in the presence of molecular iodine has been reported. This method is base and metal free and features inexpensive catalysts, with a simple procedure and a short reaction time.

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

scholarly journals Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2260
Author(s):  
Margherita Pirola ◽  
Alessandra Puglisi ◽  
Laura Raimondi ◽  
Alessandra Forni ◽  
Maurizio Benaglia
Keyword(s):  
Continuous Flow ◽  
Stereoselective Synthesis ◽  
Catalytic Reduction ◽  
Lewis Base ◽  
Crucial Point ◽  
X Ray ◽  
Metal Free ◽  
Target Molecule ◽  
Synthetic Strategy ◽  
Synthetic Sequence

A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the catalytic reduction of a fluorinated enamine with trichlorosilane as reducing agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation of the target chiral fluorinated amine in up to an 87:13 diastereoisomeric ratio.

Metal‐Free, One‐Pot Oxidative Triple Functionalization of Azaarenes with Methyl Arenes Mediated by Molecular Iodine/TBHP: Synthesis of N‐Benzylated Iodo(iso)quinolinones

2019 ◽  
Vol 8 (11) ◽  
pp. 2162-2171
Author(s):  
Bangarigalla Shantharjun ◽  
Radhakrishnan Rajeswari ◽  
Damera Vani ◽  
Ramanjaneyulu Unnava ◽  
Balasubramanian Sridhar ◽  
...  
Keyword(s):  
Molecular Iodine ◽  
One Pot ◽  
Metal Free

Metal‐Free Radical Annulation‐Hydrofunctionalization of 1,6‐Enynes for Stereoselective Synthesis of ( E )‐1‐Indanones

2020 ◽  
Vol 9 (7) ◽  
pp. 1040-1044 ◽  
Author(s):  
Ya‐Nan Wu ◽  
Tian‐Shu Zhang ◽  
Wen‐Juan Hao ◽  
Shu‐Jiang Tu ◽  
Bo Jiang
Keyword(s):  
Free Radical ◽  
Stereoselective Synthesis ◽  
Metal Free

Metal-free graphdiyne doped with sp-hybridized boron and nitrogen atoms at acetylenic sites for high-efficiency electroreduction of CO2 to CH4 and C2H4

2019 ◽  
Vol 7 (8) ◽  
pp. 4026-4035 ◽  
Author(s):  
Jia Zhao ◽  
Zhe Chen ◽  
Jingxiang Zhao
Keyword(s):  
High Selectivity ◽  
High Efficiency ◽  
Metal Free

By carefully controlling the kinds and sites of the B or N dopant, graphdiyne can be utilized as a metal-free electrocatalyst with high-efficiency and high selectivity for CO2 reduction to C1 and C2 products.

I2-Catalyzed oxidative synthesis of N,4-disubstituted quinazolines and quinazoline oxides

2019 ◽  
Vol 17 (15) ◽  
pp. 3714-3717 ◽  
Author(s):  
Nagesh Jatangi ◽  
Radha Krishna Palakodety
Keyword(s):  
Molecular Iodine ◽  
Synthetic Approach ◽  
Metal Free

An easy and efficient synthetic approach to the title compounds is described, proceeding smoothly in the presence of molecular iodine. The metal-free protocol is insensitive to air moisture, is operationally simple and broadly applicable to a variety of N,4-disubstituted quinazoline-2-amine and oxides and synthesized in good to excellent yields starting from readily available inexpensive precursors.

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