Copper-Catalyzed P-H Insertion Reactions of Sulfoxonium Ylides

2021 ◽  
Author(s):  
Xinzhi Zhang ◽  
Yangyang Zhang ◽  
Cuijian Liang ◽  
Jun Jiang
Keyword(s):  
Insertion Reaction ◽  
Insertion Reactions

A copper-catalyzed P-H insertion reaction between sulfoxonium ylides and H-phosphorus oxides has been demonstrated, furnishing α-phosphonyl carboxylate derivatives in 41-93% yields. This methodology utilizing bench-stable and thermodynamically stable sulfoxonium ylides...

scholarly journals Organocatalytic Asymmetric Synthesis of α-Amino Esters from Sulfoxonium Ylides

2021 ◽  
Author(s):  
Wengang Guo ◽  
Hai Huang ◽  
Jianwei Sun
Keyword(s):  
Asymmetric Synthesis ◽  
Insertion Reaction ◽  
Metal Catalyst ◽  
Insertion Reactions ◽  
Amino Esters ◽  
Carbene Insertion

Described here is the first organocatalytic asymmetric N−H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions....

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Theoretical study on the insertion reaction of CH(X2Π) with CH4

1997 ◽  
Vol 75 (7) ◽  
pp. 996-1001 ◽  
Author(s):  
Zhi-Xiang Wang ◽  
Ming-Bao Huang. ◽  
Ruo-Zhuang Liu
Keyword(s):  
Electron Correlation ◽  
Energy Surface ◽  
Theoretical Study ◽  
Reaction Path ◽  
Basis Sets ◽  
Insertion Reaction ◽  
Molecular Orbital Calculations ◽  
Insertion Reactions ◽  
Moller Plesset ◽  
Ch Radical

The CH + CH4 reaction has been studied by means of ab initio molecular orbital calculations incorporating electron correlation with Møller–Plesset perturbation theory up to second and fourth orders with the 6-31G(d,p) and 6-311++G(2d,p) basis sets. An energetically feasible insertion reaction path has been found in the potential energy surface that confirms the experimental proposal for the mechanism of the CH + CH4 reaction. The feature of the mechanism for the CH + CH4 insertion reaction is found to be different from the feature of the mechanisms for the CH + NH3, CH + H2O, and CH + HF insertion reactions, but somewhat similar to that for the CH2 + CH4 insertion reaction. Energetic results for the CH + CH4 reactions are in agreement with experiment. Keywords: CH radical, methane, reaction mechanism.

THEORETICAL INVESTIGATION ON THE INSERTION REACTIONS OF THE GERMYLENOIDH2GeLiFWITHRH(R=Cl,SH,PH2)

2013 ◽  
Vol 12 (03) ◽  
pp. 1350003 ◽  
Author(s):  
BING-FEI YAN ◽  
WEN-ZUO LI ◽  
YU-WEI PEI ◽  
QING-ZHONG LI ◽  
JIAN-BO CHENG
Keyword(s):  
Potential Energy ◽  
Gas Phase ◽  
Potential Energy Surfaces ◽  
Stationary Points ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Reaction Energies ◽  
Energy Surfaces ◽  
First Time ◽  
Calculated Potential Energy

The insertion reactions of the germylenoid H2GeLiF with RH (R = Cl, SH , PH2) were studied for the first time by using the DFT B3LYP and QCISD methods. The geometries of the stationary points on the potential energy surfaces of the reactions were optimized at the B3LYP/6-311+G (d,p) level of theory. The calculated results indicated that the mechanisms of the insertion reactions of H2GeLiF with HCl , H2S , and PH3are identical to each other. The QCISD/6-311++G(d,p)//B3LYP/6-311+G(d,p) calculated potential energy barriers of the three reactions are 81.80, 123.39 and 205.56 kJ/mol, and the reaction energies for the three reactions are -58.74, -33.51 and -13.35 kJ/mol, respectively. Under the same situation, the insertion reactions should occur easily in the following order H–Cl > H–SH > H–PH2. The insertion reaction in THF solution is easier than in gas phase.

scholarly journals The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions

2016 ◽  
Vol 7 (7) ◽  
pp. 4067-4072 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Jia-Jia Cao ◽  
Shun-Yi Wang ◽  
Shun-Jun Ji
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Facile Synthesis ◽  
Metal Free ◽  
Practical Synthesis

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed.

Metal-Quinoid Carbene Chemistry: From Bonding to C–H Activation Catalysis

Synlett ◽  
2020 ◽  
Author(s):  
Chi-Ming Che ◽  
Hai-Xu Wang ◽  
Kai Wu
Keyword(s):  
Hydrogen Atom ◽  
Recent Work ◽  
Hydrogen Atom Transfer ◽  
Insertion Reaction ◽  
Atom Transfer ◽  
Insertion Reactions ◽  
Dual Reactivity ◽  
Carbene Complexes ◽  
Carbene Transfer

This account summarizes our recent work on metal-quinoid carbene (QC) chemistry including (a) dirhodium-catalyzed QC C(sp2)–H insertion reactions enabled by a C-centered carbene-transfer reactivity, (b) the isolation, characterization, and dual reactivity of Ru(II) porphyrin QC complexes, and (c) iridium(III) porphyrin-catalyzed QC C(sp3)–H insertion reaction initiated by an O-centered hydrogen-atom transfer reactivity of metal–QC species.1 Introduction2 Catalytic Quinoid Carbene Insertions into C(sp2)–H Bonds Enabled by Carbene-Transfer Reactivity3 Ruthenium(II) Porphyrin Quinoid Carbene Complexes and Dual Reactivity4 Catalytic Quinoid Carbene Insertions into C(sp3)–H Bonds Enabled by Hydrogen-Atom-Transfer Reactivity5 Perspective and Outlook

Intermediate snapshot on the insertion reaction of isocyanates into the Zn–Cp* bond of dizincocene Cp*2Zn2

2020 ◽  
Vol 56 (61) ◽  
pp. 8643-8646 ◽  
Author(s):  
Bin Li ◽  
Christoph Wölper ◽  
Kevin Huse ◽  
Stephan Schulz
Keyword(s):  
Single Crystal ◽  
Insertion Reaction ◽  
X Ray Diffraction ◽  
Insertion Reactions ◽  
X Ray ◽  
Computational Calculations

Heteroleptic Zn(i) complexes Cp*Zn–Zn(N(R)C(Cp*)O) with η4-coordinated tethered Cp* ligand represent snapshots of isocyanate insertion reactions into Zn–Cp* bonds. Their bonding nature was analysed by single crystal X-ray diffraction and computational calculations.

B(C6F5)3-catalyzed O−H insertion reactions of diazoalkanes with phosphinic acids

2021 ◽  
Author(s):  
Yangyang Zhang ◽  
Xinzhi Zhang ◽  
Jincheng Zhao ◽  
Jun Jiang
Keyword(s):  
Base Metal ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Highly Efficient ◽  
Phosphinic Acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3 has been developed. This powerful methodology provides a green...

Chiral Lewis acid-catalyzed enantioselective cyclopropanation and C–H insertion reactions of vinyl ketones with α-diazoesters

2018 ◽  
Vol 54 (70) ◽  
pp. 9837-9840 ◽  
Author(s):  
Peng Zhao ◽  
Simeng Wu ◽  
Chaoqi Ke ◽  
Xiaohua Liu ◽  
Xiaoming Feng
Keyword(s):  
Lewis Acid ◽  
High Yield ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Chiral Lewis Acid ◽  
Acid Catalyzed

N,N′-Dioxide-scandium(iii) complex catalyzed cyclopropanation and C–H insertion reaction between α-substituted vinyl ketones and α-diazoesters in high yield and enantioselectivity.

scholarly journals Uncommon carbene insertion reactions

2021 ◽  
Author(s):  
Ming-Yao Huang ◽  
Shou-Fei Zhu
Keyword(s):  
Transition Metal ◽  
Insertion Reaction ◽  
Insertion Reactions ◽  
Carbene Insertion

Transition-metal-catalysed carbene insertion reaction is a straightforward and efficient protocol for the construction of carbon-carbon or carbon-heteroatom bonds. Compared to the intensively studied and well-established “common” carbene insertion reactions, including...

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