Journal ArticleDOI
Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly.
Sukdev Bag,Tuhin Patra,Atanu Modak,Arghya Deb,Soham Maity,Uttam Dutta,Aniruddha Dey,Rajesh Kancherla,Arun Maji,Avijit Hazra,Milan Bera,Debabrata Maiti +11 more
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TLDR
An easily recyclable, novel Si-containing biphenyl-based template is reported that directs efficient functionalization of the distal p-C-H bond of toluene by forming a D-shaped assembly that allows the required flexibility to support the formation of an oversized pre-transition state.Abstract:
Site-selective C-H functionalization has emerged as an efficient tool in simplifying the synthesis of complex molecules. Most often, directing group (DG)-assisted metallacycle formation serves as an efficient strategy to ensure promising regioselectivity. A wide variety of ortho- and meta-C-H functionalizations stand as examples in this regard. Yet despite this significant progress, DG-assisted selective para-C-H functionalization in arenes has remained unexplored, mainly because it involves the formation of a geometrically constrained metallacyclic transition state. Here we report an easily recyclable, novel Si-containing biphenyl-based template that directs efficient functionalization of the distal p-C-H bond of toluene by forming a D-shaped assembly. This DG allows the required flexibility to support the formation of an oversized pre-transition state. By overcoming electronic and steric bias, para-olefination and acetoxylation were successfully performed while undermining o- and m-C-H activation. The applicability of this D-shaped biphenyl template-based strategy is demonstrated by synthesizing various complex molecules.read more
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Distal meta-C–H functionalization of α-substituted cinnamates
TL;DR: In this article , a novel strategy for the palladium-catalyzed selective meta-C-H activation of α-substituted cinnamates and their heterocyclic analogues with various alkenes using nitrile as a directing group (DG) has been described.
Journal ArticleDOI
Palladium‐Catalyzed Distal CH Functionalization of Arenes
TL;DR: In this article , palladium-catalyzed distal meta- or para-C�H functionalization of arene substrates remains significant challenges owing to the unstable macrocyclic transition state.
Journal ArticleDOI
Zincate‐Mediated Remote Functionalisation of p‐Iodobenzyl Derivatives Through Metallotropy in 2‐Methyltetrahydrofuran as Key Solvent
TL;DR: In this article , the zincate-mediated remote functionalisation of p-iodobenzyl derivatives through metallotropy with a broad scope has been investigated, tolerates a wide range of sensitive functionalities within the substrates as well as enolisable and activated or deactivated aromatic aldehydes as reaction partners.
Journal ArticleDOI
Zinc Trifluoromethanesulfonate-Catalyzed para-Selective Amination of Free Anilines and Free Phenols with Quinoneimides.
Wei-Jen Lan,Jiatong Zhu,Buweihailiqiemu Abulaiti,Genyuan Chen,Zhihao Zhang,Nan Yan,Jie Wang,Xiaomei Zhang,Li-Hua Liao +8 more
TL;DR: The developed protocol offers a promising approach not only for the construction of structurally diverse p-phenylenediamine compounds with excellent yields but also for the synthesis of the para-amination of free phenol derivatives with good to excellent yields.
References
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Journal ArticleDOI
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
TL;DR: This is the first comprehensive review encompassing the large body of work in this field over the past 5 years, and will focus specifically on ligand-directed C–H functionalization reactions catalyzed by palladium.
Journal ArticleDOI
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.
TL;DR: A review of palladium-catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle can be found in this paper.
Journal ArticleDOI
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds
Charles S. Yeung,Vy M. Dong +1 more
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Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
TL;DR: This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.