Achieving Site-Selectivity for C–H Activation Processes Based on Distance and Geometry: A Carpenter’s Approach
| Autor: | Pritha Verma, Erika L. Lucas, Jin-Quan Yu, Tyler G. Saint-Denis, Nikita Chekshin, Nelson Y. S. Lam, Guangrong Meng |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Steric effects
Carboxylic Acids Organophosphonates Geometry 010402 general chemistry 01 natural sciences Biochemistry Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Molecular recognition Transition Elements Molecule Amines Molecular Structure Site selectivity Regioselectivity General Chemistry Sulfinic Acids 0104 chemical sciences chemistry Alcohols Functional group Realization (systems) |
| Zdroj: | J Am Chem Soc |
| Popis: | The ability to differentiate between highly similar C-H bonds in a given molecule remains a fundamental challenge in organic chemistry. In particular, the lack of sufficient steric and electronic differences between C-H bonds located distal to functional groups has prevented the development of site-selective catalysts with broad scope. An emerging approach to circumvent this obstacle is to utilize the distance between a target C-H bond and a coordinating functional group, along with the geometry of the cyclic transition state in directed C-H activation, as core molecular recognition parameters to differentiate between multiple C-H bonds. In this Perspective, we discuss the advent and recent advances of this concept. We cover a wide range of transition-metal-catalyzed, template-directed remote C-H activation reactions of alcohols, carboxylic acids, sulfonates, phosphonates, and amines. Additionally, we review eminent examples which take advantage of non-covalent interactions to achieve regiocontrol. Continued advancement of this distance- and geometry-based differentiation approach for regioselective remote C-H functionalization reactions may lead to the ultimate realization of molecular editing: the freedom to modify organic molecules at any site, in any order. |
| Databáze: | OpenAIRE |
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