Metal-Free O
-Selective Direct Acylation of Amino Alcohols Through Pseudo-Intramolecular Process

Metal and ligand free chemoselective reduction of keto group and complete reduction of the both keto and amide groups of α-keto amide with hydrosilanes using tetrabutylammoniumflouride (TBAF) as catalyst have been accomplished. This methodology affords an efficient and economic route for the synthesis of biologically important α-hydroxy amides and β-amino alcohols.

Download Full-text

Metal-Free α-C(sp3)–H Functionalized Oxidative Cyclization of Tertiary N,N-Diaryl Amino Alcohols: Theoretical Approach for Mechanistic Pathway

10.20944/preprints201702.0087.v1 ◽

2017 ◽

Author(s):

Zakir Ullah ◽

Mihyun Kim

Keyword(s):

Free Energy ◽

Radical Cation ◽

Theoretical Approach ◽

Dft Calculation ◽

Amino Alcohols ◽

Oxidative Cyclization ◽

Solution Phase ◽

Ionic Mechanism ◽

Metal Free ◽

Mechanistic Pathway

The mechanistic pathway of TEMPO/I2-mediated oxidative cyclization of N,N-diaryl amino alcohols 1 is investigated in this study. Based on our direct empirical experiments, three key intermediates (the aminium radical cation 3, the α-aminoalkyl radical 4, and the iminium 5), four kind reactive species (radical TEMPO, cationic TEMPO, TEMPO-I and iodo radical) and three kind pathways (1. SET/PCET mechanism, 2. HAT/1,6-H transfer mechanism, 3. Ionic mechanism) were assumed. Under the assumption, nine free energy diagrams are acquired through DFT calculation. From the comparison of the solution phase free energy, some possibility can be excluded and then the chosen plausible mechanisms are concretized with the more stable intermediate 7.

Download Full-text

A facile and efficient synthesis of β-amino alcohols using 2,2,2-trifluoroethanol as a metal-free and reusable medium

Journal of Fluorine Chemistry ◽

10.1016/j.jfluchem.2009.10.003 ◽

2010 ◽

Vol 131 (1) ◽

pp. 106-110 ◽

Cited By ~ 26

Author(s):

Samad Khaksar ◽

Akbar Heydari ◽

Mahmood Tajbakhsh ◽

Hamid Reza Bijanzadeh

Keyword(s):

Amino Alcohols ◽

Efficient Synthesis ◽

Metal Free

Download Full-text

Metal‐Free and syn‐Selective Hydrohalogenation of Alkynes through the Pseudo‐Intramolecular Process

European Journal of Organic Chemistry ◽

10.1002/ejoc.202101134 ◽

2021 ◽

Author(s):

Haruyasu Asahara ◽

Yusuke Mukaijo ◽

Kengo Muragishi ◽

Kento Iwai ◽

Akitaka Ito ◽

...

Keyword(s):

Metal Free ◽

Intramolecular Process

Download Full-text

Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening

Tetrahedron Letters ◽

10.1016/j.tetlet.2018.06.002 ◽

2018 ◽

Vol 59 (28) ◽

pp. 2748-2751 ◽

Cited By ~ 5

Author(s):

Yong-Gang Hua ◽

Qian-Qian Yang ◽

Yi Yang ◽

Mei-Jing Wang ◽

Wen-Chao Chu ◽

...

Keyword(s):

Ring Opening ◽

Amino Alcohols ◽

One Pot ◽

Metal Free

Download Full-text

The Shadow Widths of Very Small Particles are Formed Independently of the Metal Cap Build Up on the Particle

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100099283 ◽

1981 ◽

Vol 39 ◽

pp. 568-569

Author(s):

George C. Ruben

Keyword(s):

Gold Particle ◽

Film Surface ◽

Small Particles ◽

Geometric Process ◽

Metal Free ◽

Shadow Area

The formation of shadows behind small particles has been thought to be a geometric process (GP) where the metal cap build up on the particle creates a shadow width the same size as or larger than the particle. This GP cannot explain why gold particle shadow widths are generally larger than the gold particle and may have no appreciable metal cap build up (fig. 1). Ruben and Telford have suggested that particle shadow widths are formed by the width dependent deflection of shadow metal (SM) lateral to and infront of the particle. The trajectory of the deflected SM is determined by the incoming shadow angle (45°). Since there can be up to 1.4 times (at 45°) more SM directly striking the particle than the film surface, a ridge of metal nuclei lateral to and infront of the particle can be formed. This ridge in turn can prevent some SM from directly landing in the metal free shadow area. However, the SM that does land in the shadow area (not blocked by the particle or its ridge) does not stick and apparently surface migrates into the SM film behind the particle.

Download Full-text