Free-radical anti-Markovnikov hydroalkylation of unactivated alkenes with simple alkanes

2018 ◽  
Vol 20 (15) ◽  
pp. 3432-3435 ◽  
Author(s):  
Yunfei Tian ◽  
Anbo Ling ◽  
Ren Fang ◽  
Ren Xiang Tan ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Functional Group ◽  
Bond Cleavage ◽  
Site Selectivity ◽  
High Site

A Cu(ii)-mediated radical anti-Markovnikov hydroalkylation of unactivated alkenes with simple alkanes via selective C(sp3)–H bond cleavage was achieved. This reaction features high site-selectivity, diverse functional group tolerance, and scalability.

Palladium-catalyzed site-selective arylation of aliphatic ketones enabled by a transient ligand

2018 ◽  
Vol 54 (22) ◽  
pp. 2759-2762 ◽  
Author(s):  
Lei Pan ◽  
Ke Yang ◽  
Guigen Li ◽  
Haibo Ge
Keyword(s):  
Functional Group ◽  
Direct Arylation ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Palladium Catalyzed ◽  
High Site ◽  
Site Selective

A direct arylation of C–H bonds of ketones enabled by a cheap and commercially available transient ligand with high site-selectivity and functional group compatibility is reported.

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

scholarly journals Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis

2019 ◽  
Author(s):  
Byung Joo Lee ◽  
kimberly deglopper ◽  
Tehshik Yoon
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Site Selectivity ◽  
Wide Range ◽  
High Site ◽  
Alkoxy Groups ◽  
Site Selective ◽  
Mediated Oxidation

<div> <div> <div> <p>There are relatively few methods that accom- plish the selective alkoxylation of sp3-hybridized C–H bonds, particularly in comparison to the numerous analogous strate- gies for C–N and C–C bond formation. We report a photo- catalytic protocol for the functionalization of benzylic C–H bonds with a wide range of readily available oxygen nucleo- philes. Our strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C–O bonds with high site selectivity, chemoselectivity, and functional group tolerance. This method enables the late- stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential appli- cations in synthesis and medicinal chemistry. </p> </div> </div> </div>

Ru-Catalyzed highly site-selective C–H bond arylation of 9-(pyrimidin-2-yl)-9H-carbazole

RSC Advances ◽  
2016 ◽  
Vol 6 (59) ◽  
pp. 54431-54434 ◽  
Author(s):  
K. Harsha Vardhan Reddy ◽  
R. Uday Kumar ◽  
V. Prakash Reddy ◽  
G. Satish ◽  
Jagadeesh Babu Nanubolu ◽  
...  
Keyword(s):  
Functional Group ◽  
Boronic Acids ◽  
Site Selectivity ◽  
High Site ◽  
Site Selective

We describe an efficient ruthenium-catalyzed C–H bond ortho-arylation of 9-(pyrimidin-2-yl)-9H-carbazole using boronic acids. This methodology exhibits excellent and high site-selectivity, functional group tolerance and gave the desired product in moderate to good yields.

Caged iridium catalyst for hydrosilylation of alkynes with high site selectivity

ChemCatChem ◽  
2022 ◽  
Author(s):  
Qiaosheng Li ◽  
Defa Gu ◽  
Dongdong Yu ◽  
Yuzhou Liu
Keyword(s):  
Iridium Catalyst ◽  
Site Selectivity ◽  
High Site

Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C–N bond cleavage

2016 ◽  
Vol 52 (81) ◽  
pp. 12076-12079 ◽  
Author(s):  
Ming Cui ◽  
Hongxiang Wu ◽  
Junsheng Jian ◽  
Hui Wang ◽  
Chao Liu ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Cleavage ◽  
Catalyst Loading ◽  
Sonogashira Coupling ◽  
Broad Array ◽  
Palladium Catalyzed ◽  
Low Catalyst Loading

The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C–N bond. The protocol is mild, highly functional group tolerant and can be efficiently employed in the synthesis of a broad array of ynones in 48–98% yields under low catalyst loading and Cu-free conditions.

Copper-Catalyzed Intramolecular α-C–H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

Synthesis ◽  
2019 ◽  
Vol 51 (16) ◽  
pp. 3160-3170
Author(s):  
Srilaxmi M. Patel ◽  
Harika Chada ◽  
Sonali Biswal ◽  
Sonika Sharma ◽  
Duddu S. Sharada
Keyword(s):  
Ring Opening ◽  
Functional Group ◽  
Bond Cleavage ◽  
Isatoic Anhydride ◽  
General Method

A copper-catalyzed intramolecular α-C–H amination has been developed for the synthesis of quinazolin-4(3H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3H)-one was synthesized from 2-amino-N-isopropylbenzamide by C–C bond cleavage, and N-benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1H)-one along with 2-phenylquinazolin-4(3H)-one by N–C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3H)-one by copper-catalyzed intramolecular C–H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

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