scholarly journals Activation of N-hydroxy compounds by P-O bond formation through anodic oxidation of triphenylphosphine.

1980 ◽  
Vol 28 (7) ◽  
pp. 2247-2250 ◽  
Author(s):  
HIDENOBU OHMORI ◽  
SHIRO NAKAI ◽  
MASAICHIRO MASUI
Keyword(s):  
Anodic Oxidation ◽  
Bond Formation ◽  
Hydroxy Compounds

Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles

2019 ◽  
Vol 17 (14) ◽  
pp. 3482-3488 ◽  
Author(s):  
Alexander O. Terent'ev ◽  
Olga M. Mulina ◽  
Vadim D. Parshin ◽  
Vladimir A. Kokorekin ◽  
Gennady I. Nikishin
Keyword(s):  
Bond Formation ◽  
Hydroxy Compounds

A variety of sulfonates were synthesized from sulfonyl hydrazides and N-hydroxy compounds via electrochemically induced oxidative S–O bond formation.

Benzylic Intermolecular Carbon−Carbon Bond Formation by Selective Anodic Oxidation of Dithioacetals

2001 ◽  
Vol 3 (8) ◽  
pp. 1245-1248 ◽  
Author(s):  
Kazuhiro Chiba ◽  
Rikiya Uchiyama ◽  
Shokaku Kim ◽  
Yoshikazu Kitano ◽  
Masahiro Tada
Keyword(s):  
Anodic Oxidation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond

ChemInform Abstract: Benzylic Intermolecular Carbon-Carbon Bond Formation by Selective Anodic Oxidation of Dithioacetals.

ChemInform ◽  
2010 ◽  
Vol 32 (33) ◽  
pp. no-no
Author(s):  
Kazuhiro Chiba ◽  
Rikiya Uchiyama ◽  
Shokaku Kim ◽  
Yoshikazu Kitano ◽  
Masahiro Tada
Keyword(s):  
Anodic Oxidation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Biologically Active ◽  
Dft Studies ◽  
Thermodynamic Control ◽  
Important Goal ◽  
Peptide Bonds ◽  
Metal Free ◽  
Vinyl Cation ◽  
E And Z Isomers ◽  
Vinyl Fluorides

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

2018 ◽  
Author(s):  
Mohit Kapoor ◽  
Pratibha Chand-Thakuri ◽  
Michael Young
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Chelate Effect ◽  
Free Amine ◽  
Carbon Carbon Bond ◽  
New Strategy ◽  
Metal Catalyzed

Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of <i>ortho</i>-arylbenzylamines, however, effective <i>ortho</i>-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using Pd<sup>II</sup> remains an outstanding challenge. Presented herein is a new strategy for constructing <i>ortho</i>-arylated primary and secondary benzylamines mediated by carbon dioxide (CO<sub>2</sub>). The use of CO<sub>2</sub> is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

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