Selective C–C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant

2020 ◽  
Vol 56 (89) ◽  
pp. 13820-13823
Author(s):  
Sen Li ◽  
Kun Jie ◽  
Wenjie Yan ◽  
Qingjun Pan ◽  
Min Zhang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Directing Group

Herein, copper-catalyzed direct C–C bond cleavage of amides fused to 8-aminoquinoline as a directing group to form urea in the presence of amines and dioxygen is reported.

Suzuki–Miyaura coupling of unstrained ketones via chelation-assisted C–C bond cleavage

2018 ◽  
Vol 16 (39) ◽  
pp. 7174-7177 ◽  
Author(s):  
Cheng Jiang ◽  
Zhao-Jing Zheng ◽  
Tian-Yang Yu ◽  
Hao Wei
Keyword(s):  
Bond Cleavage ◽  
Catalytic Activation ◽  
Directing Group

Herein, we report that unstrained ketones can be efficiently employed as electrophiles in Suzuki–Miyaura reactions via catalytic activation of unstrained C–C bonds assist by an N-containing directing group.

Directing group migration strategy in transition-metal-catalysed direct C–H functionalization

2021 ◽  
Author(s):  
Yingtao Wu ◽  
Chao Pi ◽  
Yangjie Wu ◽  
Xiuling Cui
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Migration Strategy ◽  
Directing Group ◽  
Group Migration

In this tutorial review, the rapid advances of directing group (DG) migration in transition-metal-catalysed direct C–H activation was presented through analyzing and comparing the different bond cleavage trigger DG migration (including N–O, N–C, N–N or O–C).

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

Metal-Metal Cooperative Bond Activation by Heterobimetallic Alkyl, Aryl, and Acetylide PtII/CuI Complexes

2020 ◽  
Author(s):  
Shubham Deolka ◽  
Orestes Rivada Wheelaghan ◽  
Sandra Aristizábal ◽  
Robert Fayzullin ◽  
Shrinwantu Pal ◽  
...  
Keyword(s):  
Alkyl Group ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Terminal Alkyne ◽  
Alkyl Aryl ◽  
Metal Metal ◽  
The Stability ◽  
Selective Formation ◽  
Organoplatinum Compounds

We report selective formation of heterobimetallic PtII/CuI complexes that demonstrate how facile bond activation processes can be achieved by altering reactivity of common organoplatinum compounds through their interaction with another metal center. The interaction of the Cu center with Pt center and with a Pt-bound alkyl group increases the stability of PtMe2 towards undesired rollover cyclometalation. The presence of the CuI center also enables facile transmetalation from electron-deficient tetraarylborate [B(ArF)4]- anion and mild C-H bond cleavage of a terminal alkyne, which was not observed in the absence of an electrophilic Cu center. The DFT study indicates that the role of Cu center acts as a binding site for alkyne substrate, while activating its terminal C-H bond.

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