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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Palladium-Catalyzed Late-Stage ortho-C–H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group
TL;DR: In this paper, a methodology for the late stage ortho-C-H bond aroylation of anilines with aryl aldehydes led to a variety of orthoaroylated aniline by the use of palladium(II) acetate, tert-butyl hydroperoxide, and 1,4-dioxane as the catalyst, oxidant, and solvent, respectively.
Journal ArticleDOI
Sustainable C-H functionalizations under ball-milling, microwave-irradiation and aqueous media
Ranjini Laskar,Tanay Pal,Trisha Bhattacharya,Siddhartha Maiti,Munetaka Akita,Debabrata Maiti +5 more
TL;DR: Transition metal mediated C-H functionalizations have been a relevant realm in organic synthesis for decades, but sustainability as an inherent feature in such transformations remains under-explored.
Journal ArticleDOI
PdCl2(CH3CN)2-catalyzed regioselective C-H olefinations of 2-amino biaryls with vinylsilanes as unactivated alkenes.
TL;DR: The first example of palladium-catalyzed chelation-assisted C-H olefination of 2-amino biaryls using readily available vinylsilanes as unactivated oleFinating reagents has been developed, affording valuable arylated vinylsilane compounds in moderate to excellent yields and with exclusive (E)-selectivities.
Journal ArticleDOI
Palladium-catalyzed remote para-C-H activation of arenes assisted by a recyclable pyridine-based template.
TL;DR: An unprecedented pyridine-based para-directing template (DT) assisted, Pd-catalyzed para-C–H alkenylation of three classes of arenes, i.e. phenylpropanoic acids, 2-phenyl benzoic acids and benzyl alcohols, with a series of alkenes including perfluoroalkenes is reported.
Journal ArticleDOI
para-Selective C–H bond functionalization of iodobenzenes
TL;DR: An oxidation-induced strategy for para-selective C-H bond functionalization of iodobenzenes towards the synthesis of various useful asymmetric diaryl ethers was demonstrated and a general idea for the development of new, highly selective para-C-H functionalization reactions is proposed.
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.