NHC ligand-powered palladium-catalyzed carbonylative C–S bond cleavage of vinyl sulfides: efficient access to tert-butyl arylacrylates

2020 ◽  
Vol 18 (48) ◽  
pp. 9796-9799
Author(s):  
Jian-Xing Xu ◽  
Fengqian Zhao ◽  
Xiao-Feng Wu
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Tert Butyl ◽  
Efficient Access ◽  
Vinyl Sulfides ◽  
Palladium Catalyzed

A palladium-catalyzed carbonylative C–S bond activation of divinyl sulfides to synthesize various tert-(E)-butyl arylacrylates under 1 bar of CO has been developed. A series of tert-(E)-butyl acrylates were obtained in moderate to good yields.

Palladium-catalyzed C(carbonyl)–C bond cleavage of amides: a facile access to phenylcarbamate derivatives with alcohols

2018 ◽  
Vol 54 (62) ◽  
pp. 8606-8609 ◽  
Author(s):  
Xufei Yan ◽  
Huihui Sun ◽  
Haifeng Xiang ◽  
Da-Gang Yu ◽  
Daibing Luo ◽  
...  
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Palladium Catalyzed ◽  
Sulfur Containing

A sulfur-containing auxiliary enabled palladium-catalyzed C(carbonyl)–C bond activation of amides was reported to form phenylcarbamate derivatives with alcohols.

Palladium-catalyzed C–S bond activation and functionalization of 3-sulfenylindoles and related electron-rich heteroarenes

2017 ◽  
Vol 4 (8) ◽  
pp. 1590-1594 ◽  
Author(s):  
Jianxiao Li ◽  
Yanni An ◽  
Jiawei Li ◽  
Shaorong Yang ◽  
Wanqing Wu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Palladium Catalyzed

A novel palladium-catalyzed approach for constructing functionalized heteroarenes via C–S bond cleavage and C–C bond formation has been demonstrated.

Synthesis of Phenanthridinones by Palladium-Catalyzed Cyclization of N-Aryl-2-aminopyridines with 2-Iodobenzoic Acids in Water

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 280-284
Author(s):  
Xiaojuan Ding ◽  
Lei Zhang ◽  
Yiyang Mao ◽  
Binsen Rong ◽  
Ning Zhu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Efficient Access ◽  
Palladium Catalyzed

The first Pd-catalyzed cyclization of N-aryl-2-aminopyridines with 2-iodobenzoic acids for the synthesis of phenanthridinones through C–H bond activation under very low catalyst loadings (down to 0.1 mol% Pd) in water is reported. This protocol features a broad substrate scope and provides easy efficient access to various phenanthridinones.

N-Acylsuccinimides: twist-controlled, acyl-transfer reagents in Suzuki–Miyaura cross-coupling by N–C amide bond activation

2017 ◽  
Vol 15 (42) ◽  
pp. 8867-8871 ◽  
Author(s):  
Yuki Osumi ◽  
Chengwei Liu ◽  
Michal Szostak
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Amide Bond ◽  
Acyl Transfer ◽  
Palladium Catalyzed

The palladium-catalyzed Suzuki–Miyaura cross-coupling of N-acylsuccinimides as versatile acyl-transfer reagents via selective amide N–C bond cleavage is reported.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation

2018 ◽  
Vol 16 (17) ◽  
pp. 3099-3103 ◽  
Author(s):  
Weijie Yu ◽  
Shuwu Yang ◽  
Fei Xiong ◽  
Tianxiang Fan ◽  
Yan Feng ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
First Time ◽  
Acid Esters

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C–N bond cleavage.

Palladium-catalysed alkenyl and carbonylative C-C bond activation of cyclobutanones

2021 ◽  
Author(s):  
Chen Chen ◽  
Haixia Zhao ◽  
Yue Pu ◽  
Lulu Tang ◽  
Jian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Bond Cleavage ◽  
Palladium Catalyzed

A palladium catalyzed C-C bond activation of cyclobutanones for the construction of alkenyl and carbonylated indanones has been developed. The insitu generated σ-alkylpalladium intermediate via C-C bond cleavage of cyclobutanone...

Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp3 C–H bond activation

2014 ◽  
Vol 50 (73) ◽  
pp. 10699-10702 ◽  
Author(s):  
Ying Xie ◽  
Tengfei Chen ◽  
Shaomin Fu ◽  
Xing-Shu Li ◽  
Yuanfu Deng ◽  
...  
Keyword(s):  
Bond Activation ◽  
Efficient Access ◽  
Palladium Catalyzed

The palladium-catalyzed oxidative [3+2] cycloaddition of ketoimines with alkynes provided an efficient access to multisubstituted pyrroles via Csp3–H activation.

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.

Theoretical and experimental studies of palladium-catalyzed site-selective C(sp3)−H bond functionalization enabled by transient ligands

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Theoretical Calculations ◽  
Experimental Studies ◽  
Bond Functionalization ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

Transition metal-catalyzed selective C–H bond functionalization enabled by transient ligands has become an extremely attractive topic due to its economical and greener characteristics. However, catalytic pathways of this reaction process on unactivated sp<sup>3</sup> carbons of reactants have not been well studied yet. Herein, detailed mechanistic investigation on Pd-catalyzed C(sp<sup>3</sup>)–H bond activation with amino acids as transient ligands has been systematically conducted. The theoretical calculations showed that higher angle distortion of C(sp2)-H bond over C(sp3)-H bond and stronger nucleophilicity of benzylic anion over its aromatic counterpart, leading to higher reactivity of corresponding C(sp<sup>3</sup>)–H bonds; the angle strain of the directing rings of key intermediates determines the site-selectivity of aliphatic ketone substrates; replacement of glycine with β-alanine as the transient ligand can decrease the angle tension of the directing rings. Synthetic experiments have confirmed that β-alanine is indeed a more efficient transient ligand for arylation of β-secondary carbons of linear aliphatic ketones than its glycine counterpart.<br><br>

Sign in / Sign up

Export Citation Format

Share Document