From C4 to C7: Innovative Strategies for Site-Selective Functionalization of Indole C–H Bonds

2021 ◽  
Vol 54 (7) ◽  
pp. 1723-1736
Author(s):  
Jian Wen ◽  
Zhuangzhi Shi
Keyword(s):  
Innovative Strategies ◽  
Selective Functionalization ◽  
Site Selective

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

Switchable Reactivity: The Site-Selective Functionalization of Trifluoromethyl-Substituted Pyrazoles

2002 ◽  
Vol 2002 (17) ◽  
pp. 2913-2920 ◽  
Author(s):  
Manfred Schlosser ◽  
Jean-Noël Volle ◽  
Frédéric Leroux ◽  
Kurt Schenk
Keyword(s):  
Selective Functionalization ◽  
Site Selective ◽  
Substituted Pyrazoles

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

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

scholarly journals Site-selective remote C(sp3)–H heteroarylation of amides via organic photoredox catalysis

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Hui Chen ◽  
Wenjing Fan ◽  
Xiang-Ai Yuan ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Room Temperature ◽  
Ph Value ◽  
Metal Free ◽  
Selective Functionalization ◽  
Site Selectivity ◽  
Hydrogen Atom Transfers ◽  
Site Selective ◽  
Neutral Conditions ◽  
Potential Complement

Abstract Radical translocation processes triggered by nitrogen-centered radicals (NCRs), such as 1,5-hydrogen atom transfers (1,5-HAT), demonstrated by the well-established Hofmann-Löffler-Freytag (HLF) reaction, provide an attractive approach for the controllable and selective functionalization of remote inert C(sp3)–H bonds. Here we report an amidyl radical-triggered site-selective remote C(sp3)–H heteroarylation of amides under organic photoredox conditions. This approach provides a mild and highly regioselective reaction affording remote C(sp3)–H heteroarylated amides at room temperature under transition-metal free, weakly basic, and redox-neutral conditions. Non-prefunctionalized heteroarenes, such as purines, thiazolopyridines, benzoxazole, benzothiazoles, benzothiophene, benzofuran, thiazoles and quinoxalines, can be alkylated directly. Sequential and orthogonal C–H functionalization of different heteroarenes by taking advantage pH value or polarity of radicals has also been achieved. DFT calculations explain and can predict the site-selectivity and reactivity of this reaction. This strategy expands the scope of the Minisci reaction and serves as its alternative and potential complement.

Site-Selective Functionalization of Linear Diterpenoids through U-Shaped Folding in a Confined Artificial Cavity

2019 ◽  
Vol 141 (13) ◽  
pp. 5112-5115 ◽  
Author(s):  
Hiroki Takezawa ◽  
Tomoya Kanda ◽  
Hikaru Nanjo ◽  
Makoto Fujita
Keyword(s):  
Selective Functionalization ◽  
Artificial Cavity ◽  
Site Selective

scholarly journals C(5) Site-Selective Functionalization of (S)-Cotinine

2017 ◽  
Vol 83 (1) ◽  
pp. 516-520
Author(s):  
Hugo Rego Campello ◽  
Timothy Gallagher
Keyword(s):  
Selective Functionalization ◽  
Site Selective

scholarly journals Exploiting structural and conformational effects for a site-selective lithiation of azetidines

2016 ◽  
Vol 88 (7) ◽  
pp. 631-648 ◽  
Author(s):  
Giovanna Parisi ◽  
Marina Zenzola ◽  
Emanuela Capitanelli ◽  
Claudia Carlucci ◽  
Giuseppe Romanazzi ◽  
...  
Keyword(s):  
Chemical Space ◽  
Molecular Structures ◽  
Structural Factors ◽  
Factors Affecting ◽  
Selective Functionalization ◽  
Conformational Effects ◽  
Conformational Preferences ◽  
A Site ◽  
Site Selective

AbstractInterest in molecular structures bearing four-membered heterocycles (FMHs) is growing due to the possibility to explore new regions of the chemical space and get new lead molecules. Our interest in the development of divergent synthesis of functionalized FMHs, prompted us to disclose factors affecting the reactivity of nitrogen-bearing FMHs towards metalating agents. Our investigations demonstrated that structural factors and conformational preferences need to be considered in planning a site-selective functionalization of azetidines. It will be showed how such factors could have pivotal importance in the reactivity of FMHs.

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