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-alkenylation of formal amines enabled by catalytic use of hydrogen-bonding anionic ligands
Nupur Goswami,Soumya Kumar Sinha,Partha Palit Dhrubojyoti Mukherjee Poulami Mahanta Subhash C Mondal,Sankar Adhya,Ayan Datta,Debabrata Maiti +5 more
TL;DR: Mondal et al. as discussed by the authors proposed a Pd-catalyzed meta-selective C-H functionalization of simple amines by harnessing weak non-covalent interactions between an anionic ligand and neutral substrate.
Journal ArticleDOI
Palladium‐Catalyzed para‐C−H Arylation of Anilines with Aromatic Halides
Dominik Lichte,Nico Pirkl,Gregor Heinrich,Sayan Dutta,Jonas Felix Goebel,Debasis Koley,Lukas J. Goossen +6 more
TL;DR: This work demonstrates how the para -C-H arylation of anilines with non-activated aryl halides, elusive to date, is achieved by a base-assisted "metalla-tautomerism" approach.
Journal ArticleDOI
Predictable site-selective functionalization: Promoter group assisted para-halogenation of N-substituted (hetero)aromatics under metal-free condition
Shiv Shankar Gupta,Manisha,Manisha,Rakesh Kumar,Rakesh Kumar,Ankit Kumar Dhiman,Ankit Kumar Dhiman,Upendra Sharma,Upendra Sharma +8 more
TL;DR: In this paper, the pyrimidyl group is identified as a reactivity tuner that also controls the regioselectivity of the SEAr type reaction for the C5-bromination of indolines (para-selective) with N-Bromosuccinimide under metal and additive-free conditions.
Journal ArticleDOI
Selenium-Directed Ortho C–H Activation of Benzyl Selenide by a Selenated NHC–Half-Pincer Ruthenium(II) Complex
Sangeeta Kumari,Charu Sharma,Naveen Satrawala,Avanish Kumar Srivastava,Kamal Nayan Sharma,Raj K. Joshi +5 more
TL;DR: In this article , a selenium-directed ortho-vinylation of benzyl selenide using a Ru(II) catalyst was reported, which is the first report on benzyl SE functionalization.
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
Journal ArticleDOI
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.