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Title: Selective Organic and Organometallic Reactions in Water-Soluble Host-Guest Supramolecular Systems

Abstract

Inspired by the efficiency and selectivity of enzymes, synthetic chemists have designed and prepared a wide range of host molecules that can bind smaller molecules with their cavities; this area has become known as 'supramolecular' or 'host-guest' chemistry. Pioneered by Lehn, Cram, Pedersen, and Breslow, and followed up by a large number of more recent investigators, it has been found that the chemical environment in each assembly - defined by the size, shape, charge, and functional group availability - greatly influences the guest-binding characteristics of these compounds. In contrast to the large number of binding studies that have been carried out in this area, the exploration of chemistry - especially catalytic chemistry - that can take place inside supramolecular host cavities is still in its infancy. For example, until the work described here was carried out, very few examples of organometallic reactivity inside supramolecular hosts were known, especially in water solution. For that reason, our group and the group directed by Kenneth Raymond decided to take advantage of our complementary expertise and attempt to carry out metal-mediated C-H bond activation reactions in water-soluble supramolecular systems. This article begins by providing background from the Raymond group in supramolecular coordination chemistry andmore » the Bergman group in C-H bond activation. It goes on to report the results of our combined efforts in supramolecular C-H activation reactions, followed by extensions of this work into a wider range of intracavity transformations.« less

Authors:
; ;
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
Chemical Sciences Division
OSTI Identifier:
952577
Report Number(s):
LBNL-1175E
TRN: US201002%%1482
DOE Contract Number:  
DE-AC02-05CH11231
Resource Type:
Technical Report
Country of Publication:
United States
Language:
English
Subject:
37; AQUEOUS SOLUTIONS; AVAILABILITY; CAVITIES; CHEMISTRY; EFFICIENCY; ENVIRONMENT; ENZYMES; EXPLORATION; FUNCTIONALS; HOST; MOLECULES; RANGE; REACTIVITY; SHAPE; SIZE; TRANSFORMATIONS

Citation Formats

Pluth, Michael D, Raymond, Kenneth N, and Bergman, Robert G. Selective Organic and Organometallic Reactions in Water-Soluble Host-Guest Supramolecular Systems. United States: N. p., 2008. Web. doi:10.2172/952577.
Pluth, Michael D, Raymond, Kenneth N, & Bergman, Robert G. Selective Organic and Organometallic Reactions in Water-Soluble Host-Guest Supramolecular Systems. United States. https://doi.org/10.2172/952577
Pluth, Michael D, Raymond, Kenneth N, and Bergman, Robert G. Sat . "Selective Organic and Organometallic Reactions in Water-Soluble Host-Guest Supramolecular Systems". United States. https://doi.org/10.2172/952577. https://www.osti.gov/servlets/purl/952577.
@article{osti_952577,
title = {Selective Organic and Organometallic Reactions in Water-Soluble Host-Guest Supramolecular Systems},
author = {Pluth, Michael D and Raymond, Kenneth N and Bergman, Robert G},
abstractNote = {Inspired by the efficiency and selectivity of enzymes, synthetic chemists have designed and prepared a wide range of host molecules that can bind smaller molecules with their cavities; this area has become known as 'supramolecular' or 'host-guest' chemistry. Pioneered by Lehn, Cram, Pedersen, and Breslow, and followed up by a large number of more recent investigators, it has been found that the chemical environment in each assembly - defined by the size, shape, charge, and functional group availability - greatly influences the guest-binding characteristics of these compounds. In contrast to the large number of binding studies that have been carried out in this area, the exploration of chemistry - especially catalytic chemistry - that can take place inside supramolecular host cavities is still in its infancy. For example, until the work described here was carried out, very few examples of organometallic reactivity inside supramolecular hosts were known, especially in water solution. For that reason, our group and the group directed by Kenneth Raymond decided to take advantage of our complementary expertise and attempt to carry out metal-mediated C-H bond activation reactions in water-soluble supramolecular systems. This article begins by providing background from the Raymond group in supramolecular coordination chemistry and the Bergman group in C-H bond activation. It goes on to report the results of our combined efforts in supramolecular C-H activation reactions, followed by extensions of this work into a wider range of intracavity transformations.},
doi = {10.2172/952577},
url = {https://www.osti.gov/biblio/952577}, journal = {},
number = ,
volume = ,
place = {United States},
year = {2008},
month = {2}
}