Computational I(III)-X BDEs for Benziodoxol(on)e-based Hypervalent Iodine Reagents: Implications for Their Functional Group Transfer Abilities

2019 ◽  
Vol 37 (4) ◽  
pp. 359-363 ◽  
Author(s):  
Jin-Dong Yang ◽  
Man Li ◽  
Xiao-Song Xue
Keyword(s):  
Functional Group ◽  
Hypervalent Iodine ◽  
Group Transfer

scholarly journals Gold and hypervalent iodine(iii): liaisons over a decade for electrophilic functional group transfer reactions

2020 ◽  
Vol 56 (18) ◽  
pp. 2677-2690 ◽  
Author(s):  
Somsuvra Banerjee ◽  
Vivek W. Bhoyare ◽  
Nitin T. Patil
Keyword(s):  
Functional Group ◽  
Transfer Reactions ◽  
Hypervalent Iodine ◽  
Group Transfer

Building on mechanistic perspective, the review intends to demonstrate how the uniqueness of Au-catalysts has realized a myriad of electrophilic functional group transfer reactions with the use of hypervalent iodine(iii) reagents over the last decade.

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

2020 ◽  
Vol 59 (24) ◽  
pp. 9264-9280 ◽  
Author(s):  
Simon L. Rössler ◽  
Benson J. Jelier ◽  
Emmanuel Magnier ◽  
Guillaume Dagousset ◽  
Erick M. Carreira ◽  
...  
Keyword(s):  
Functional Group ◽  
Pyridinium Salts ◽  
Group Transfer ◽  
Active Functional Group ◽  
Redox Active

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

scholarly journals Methyl Radical Initiated Kharasch and Related Reactions

2020 ◽  
Author(s):  
Nicholas Tappin ◽  
Philippe Renaud
Keyword(s):  
Halogen Atom ◽  
Functional Group ◽  
Chain Process ◽  
Methyl Radicals ◽  
Methyl Radical ◽  
Reaction Conditions ◽  
Alternative Source ◽  
Group Transfer ◽  
Radical Trap ◽  
Flash Column Chromatography

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-<i>tert</i>-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N<sub>2</sub>) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2.0 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-<i>tert</i>-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of <i>tert-</i>butoxyl radicals to initiate these reactions under identical conditions which gives gaseous byproducts (CO<sub>2</sub>).

Pd(ii) catalyzed ortho C–H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents

2015 ◽  
Vol 51 (49) ◽  
pp. 10014-10017 ◽  
Author(s):  
Xiuyun Sun ◽  
Xia Yao ◽  
Chao Zhang ◽  
Yu Rao
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Weak Coordination ◽  
Unique Mechanism

The first example to access ortho iodinated phenols using cyclic hypervalent iodine(iii) reagents through palladium(ii) catalyzed C–H activation has been developed via weak coordination. The reaction showed excellent regioselectivity, reactivity and good functional group tolerance. A unique mechanism was proposed.

scholarly journals Methyl Radical Initiated Kharasch and Related Reactions

2020 ◽  
Author(s):  
Nicholas Tappin ◽  
Philippe Renaud
Keyword(s):  
Halogen Atom ◽  
Functional Group ◽  
Chain Process ◽  
Methyl Radicals ◽  
Methyl Radical ◽  
Reaction Conditions ◽  
Alternative Source ◽  
Group Transfer ◽  
Radical Trap ◽  
Flash Column Chromatography

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-<i>tert</i>-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N<sub>2</sub>) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2.0 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-<i>tert</i>-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of <i>tert-</i>butoxyl radicals to initiate these reactions under identical conditions which gives gaseous byproducts (CO<sub>2</sub>).

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