Debabrata Maiti (editor) - Remote C-H Bond Functionalizations: Methods and Strategies in Organic Synthesis

1. Chapter 3
2. Chapter 12
3. Chapter 13

1. Chapter 2
2. Chapter 3
3. Chapter 4
4. Chapter 5
5. Chapter 6
6. Chapter 7
7. Chapter 8
8. Chapter 9
9. Chapter 10
10. Chapter 11
11. Chapter 12
12. Chapter 13

Remote CH Bond Functionalizations

Edited by

Debabrata Maiti
Srimanta Guin

Editors

Debabrata Maiti

Indian Institute of Technology Bombay

Department of Chemistry

Main Gate Rd, IIT Area

400076 Powai, Mumbai

India

Srimanta Guin

Indian Institute of Technology Bombay

Department of Chemistry

Main Gate Rd, IIT Area

400076 Powai, Mumbai

India

Cover

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Print ISBN: 9783527346677

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Uttam Dutta, Srimanta Guin, and Debabrata Maiti

Indian Institute of Technology Bombay, Department of Chemistry, Powai, Mumbai, 400076, India

Innovation and implementation of science and technology is a defining parameter to determine the progress of a civilization. Inquisitive minds are constantly devoted in empowering the human civilization by elegant discoveries and their subsequent applications in practical life. Organic chemistry, being a prime component of modern science, has served the human society in a way that has pronounced to be a boon for the present era. In one hand organic chemistry has unfolded the mechanistic intricacies of biorelevant reactivity, while on the other hand it has uncovered the methods to synthesize the molecular architecture that can either mimic the biological activity or can alter the same. Additionally, organic chemistry has profound industrial application including agrochemicals, food industry, dyes industry, polymer industry, and so on. As a whole, organic chemistry has become an inseparable component in our daily life. However, the genesis of these applications and large scale synthesis used to be initiated at synthetic laboratory. The ground breaking discoveries by erudite chemist have thus proved the intellectual supremacy of human race. However, the efficacy of synthetic methods is dependent on the step economy, atom economy, and environment benignity. Never ending aspiration to search such fruitful methods continues to challenge the chemist and inspire new chemical transformations. Accounting these existing literature precedents in the form of a concise summary, which would be the tutorial resources for future generation to accomplish successive progress, is undeniably one of the best efforts to intensify the expansion of chemical synthesis.

CH bond being the fundamental backbone of organic compounds, the potential of a CH functionalization to amend a molecule overrides traditional routes on grounds of step and atom economy. This has triggered the development of various strategies with the aim to alter the physicochemical properties of specific compounds or add on molecular complexity. Irrespective of aliphatic or aromatic setup, the CH bonds, vicinal to a functional group, are relatively easier to functionalize either by exploiting its acidity or by taking the advantage of its coordinating ability to the metal. Moving further toward distal positions, CH functionalization is engrossed with several issues including the intrinsic inertness as well as regioselectivity due to the overabundance of multiple CH bonds with subtle reactivity differences. Therefore, a curious quest was always followed to execute distal CH functionalization with precise site selectivity. In its itinerary thus far, a number of elegant approaches have been conceived to install functional group at distal location with precise and predictable selectivity. In this book, an attempt is made to provide a broad overview on contemporary advancements in the field of distal CH functionalization. Eminent researchers, who are known for their significant contributions in distinguished research areas, have penned down their collective efforts to outline a coherent and comprehensive discussion about different strategies for distal CH functionalization.

introduces to the realm of directing group ( DG ) assisted distal arene metafunctionalization. Precise control on regioselectivity is one of the most important aspects in arene CH functionalization. Arenes bearing heteroatom containing functionality, which is famously known as directing group (DG), were extensively exploited for proximal orthoCH activation. Extending such DGassisted distal metafunctionalization strategy required proper template engineering that would ensure the metaselective CH activation. In this context, Yu and coworkers disclosed a Ushaped template for metaselective alkenylation. Thereafter, Yu, Maiti, Tan, Li, and others embarked on exploring the scope of metafunctionalizations employing several templates. Gao and Li have collectively penned down in delineating a monograph on recent development of transition metalcatalyzed, template assisted distal metaCH functionalization.

was devoted in portraying synthetic applicability of the PdNBE cooperative catalysis.

The seminal work by Catellani on difunctionalization of aryl (pseudo)halides evolved in 1997. In later years, enormous efforts have been devoted in expanding the scope of this PdNBE cooperative catalysis in a relayed CH activation process. In this context, Dong and Yu independently pioneered a directing group assisted