Nickel-Catalyzed C–H Bond Functionalization Utilizing an N,N′-Bidentate Directing Group

2015 ◽  
pp. 19-46 ◽  
Author(s):  
Naoto Chatani
Keyword(s):  
Bond Functionalization ◽  
Directing Group

scholarly journals N-Benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide

Molbank ◽  
10.3390/m1075 ◽  
2019 ◽  
Vol 2019 (3) ◽  
pp. M1075 ◽  
Author(s):  
Hamad H. Al Mamari ◽  
Nasser Al Awaimri ◽  
Yousuf Al Lawati
Keyword(s):  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Title Compound ◽  
Structural Motif ◽  
Spectroscopic Methods ◽  
Bond Functionalization ◽  
Directing Group ◽  
Metal Catalyzed

The title compound, N-benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide (1) was synthesized by reacting 3-trifluoromethylbenzoyl chloride (4) and 4-aminobenzo[c][1,2,5]thiadiazole (5). The compound was characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS) and its composition confirmed by elemental analysis. The importance of this compound lies in its possession of an N,N-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C-H bond functionalization reactions.

Remote meta C–H bond functionalization of 2-phenethylsulphonic acid and 3-phenylpropanoic acid derivatives

2016 ◽  
Vol 52 (96) ◽  
pp. 13916-13919 ◽  
Author(s):  
Atanu Modak ◽  
Anirban Mondal ◽  
Rahul Watile ◽  
Semanti Mukherjee ◽  
Debabrata Maiti
Keyword(s):  
Bond Activation ◽  
Acid Moiety ◽  
Bond Functionalization ◽  
Directing Group ◽  
Weakly Coordinating

This discovery illustrates selective meta C–H bond activation from multiple non-equivalent C–H bonds present in medicinally relevant arylethanesulfonic acid and the 2-arylpropanoic acid moiety using weakly coordinating nitrile as a directing group.

scholarly journals Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

2008 ◽  
Vol 130 (40) ◽  
pp. 13285-13293 ◽  
Author(s):  
Lopa V. Desai ◽  
Kara J. Stowers ◽  
Melanie S. Sanford
Keyword(s):  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Directing Group

Rhodium-Catalyzed Reductive Cleavage of Aryl Carbamates Using Isopropanol as a Reductant

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2569-2572 ◽  
Author(s):  
Naoto Chatani ◽  
Mamoru Tobisu ◽  
Kosuke Yasui ◽  
Masaya Higashino
Keyword(s):  
Functional Group ◽  
Reductive Cleavage ◽  
Bond Functionalization ◽  
Directing Group ◽  
Catalyzed Reactions

Despite the widespread use of carbamates as a directing group in C–H bond-functionalization reactions, reductive removal of this directing group is not straightforward. Currently available methods are limited to nickel-catalyzed reactions using i PrMgX or hydrosilane as a reductant, leaving the functional group compatibility issue to be solved. Herein, we report rhodium-catalyzed reductive cleavage of aryl carbamates using iPrOH as a milder reductant.

scholarly journals N-(2-Hydroxy-1,1-dimethylethyl)-3-methylbenzamide

Molbank ◽  
10.3390/m1099 ◽  
2019 ◽  
Vol 2020 (1) ◽  
pp. M1099 ◽  
Author(s):  
Hamad H. Al Mamari ◽  
Yousuf Al Lawati
Keyword(s):  
Elemental Analysis ◽  
13C Nmr ◽  
Present Report ◽  
Structural Motif ◽  
Spectroscopic Methods ◽  
Target Compound ◽  
Bond Functionalization ◽  
X Ray ◽  
Directing Group ◽  
Metal Catalyzed

The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed by elemental analysis, and its structure determined and confirmed by X-ray analysis. The importance of this compound lies in its possession of an N,O-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C–H bond functionalization reactions.

C8–H bond activation vs. C2–H bond activation: from naphthyl amines to lactams

2016 ◽  
Vol 52 (90) ◽  
pp. 13307-13310 ◽  
Author(s):  
Renyi Shi ◽  
Lijun Lu ◽  
Hangyu Xie ◽  
Jingwen Yan ◽  
Ting Xu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Amine Group ◽  
Easy Method ◽  
Bond Functionalization ◽  
Directing Group

Pd-catalyzed selective amine-oriented C8–H bond functionalization/N-dealkylative carbonylation of naphthyl amines has been achieved. The amine group from dealkylation is proposed to be the directing group for promoting this process. It represents a straightforward and easy method to access various biologically important benzo[cd]indol-2(1H)-one derivatives.

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