Selective functionalization of benzylic C-H bonds of two different benzylic ethers by bowl-shaped N-hydroxyimide derivatives as efficient organoradical catalysts

2022 ◽  
Author(s):  
Terumasa Kato ◽  
Keiji Maruoka
Keyword(s):  
Highly Efficient ◽  
Selective Functionalization ◽  
Synthetic Utility ◽  
Benzylic Ether ◽  
Diethyl Azodicarboxylate ◽  
Site Selective

A highly efficient, site-selective benzylic C-H bond amination of two different benzylic ether substrates was described by using bowl-shaped N-hydroxyimide organoradical catalysts with diethyl azodicarboxylate. The synthetic utility of this...

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

scholarly journals Correction to “Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols”

ACS Catalysis ◽  
2021 ◽  
pp. 10478-10478
Author(s):  
Shiyi Yang ◽  
Weiping Tang ◽  
Zhanhui Yang ◽  
Jiaxi Xu
Keyword(s):  
Highly Efficient ◽  
Site Selective ◽  
Selective Deoxygenation

scholarly journals Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Wei Jie Teo ◽  
Xiaoxu Yang ◽  
Yeng Yeng Poon ◽  
Shaozhong Ge
Keyword(s):  
Building Blocks ◽  
Mechanistic Studies ◽  
Deuterium Labeling ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Synthetic Utility ◽  
Reaction Proceeds ◽  
Site Selective ◽  
And Control ◽  
Allylic Ethers

Abstract Polyborylated organic compounds have been emerging as versatile building blocks in chemical synthesis. Here we report a selective cobalt-catalyzed deoxygenative 1,1,3-triborylation reaction of allylic ethers with pinacolborane to prepare 1,1,3-triborylalkane compounds. With naturally abundant and/or synthetic cinnamic methyl ethers as starting materials, we have achieved the synthesis of a variety of 1,1,3-triborylalkanes (25 examples). The synthetic utility of these 1,1,3-triborylalkanes is demonstrated through site-selective allylation, protodeborylation, and consecutive carbon-carbon bond-forming reactions. Mechanistic studies including deuterium-labeling and control experiments suggest that this 1,1,3-triborylation reaction proceeds through initial cobalt-catalyzed deoxygenative borylation of allylic ethers to form allylic boronates followed by cobalt-catalyzed 1,1-diborylation of the resulting allylic boronates.

scholarly journals Total Synthesis of Ellagitannins via Sequential Site-Selective Functionalization of Unprotected D-Glucose

2017 ◽  
Vol 65 (1) ◽  
pp. 25-32 ◽  
Author(s):  
Hironori Takeuchi ◽  
Yoshihiro Ueda ◽  
Takumi Furuta ◽  
Takeo Kawabata
Keyword(s):  
Total Synthesis ◽  
Selective Functionalization ◽  
Site Selective

scholarly journals Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations

2015 ◽  
Vol 51 (55) ◽  
pp. 11130-11133 ◽  
Author(s):  
S. Hörner ◽  
C. Uth ◽  
O. Avrutina ◽  
H. Frauendorf ◽  
M. Wiessler ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Site Selective ◽  
Electron Demand

A modular bioconjugation strategy based on stepwise oxime ligation and inverse electron-demand Diels–Alder reaction.

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018 ◽  
Vol 118 (23) ◽  
pp. 11457-11517 ◽  
Author(s):  
Victoria Dimakos ◽  
Mark S. Taylor
Keyword(s):  
Hydroxyl Groups ◽  
Selective Functionalization ◽  
Site Selective
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