The DOI matches its Crossref record; 180 of the 180 references it cites were found in a registry or an index.
HFIP in Organic Synthesis
Abstract
1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C-H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.
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Cites
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
Lyons, T. W., & Sanford, M. S. (2010) · Chemical Reviews · doi:10.1021/cr900184e · Cited by 6,119
Solvatochromic Dyes as Solvent Polarity Indicators
Reichardt, C. (1994) · Chemical Reviews · doi:10.1021/cr00032a005 · Cited by 5,527
Solvents and Solvent Effects in Organic Chemistry
Reichardt, C., & Welton, T. (2010) · Wiley eBooks · doi:10.1002/9783527632220 · Cited by 4,280
An overview of N-heterocyclic carbenes
Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014) · Nature · doi:10.1038/nature13384 · Cited by 4,264
Kamlet, M. J., Abboud, J. L. M., Abraham, M. H., & Taft, R. W. (1983) · The Journal of Organic Chemistry · doi:10.1021/jo00165a018 · Cited by 3,428
CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals
Yamaguchi, J., Yamaguchi, A. D., & Itami, K. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201201666 · Cited by 2,987
Cho, S. H., Kim, J. Y., Kwak, J., & Chang, S. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15082k · Cited by 2,358
Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups
Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., & Zhang, Y. (2015) · Organic Chemistry Frontiers · doi:10.1039/c5qo00004a · Cited by 1,533
C–H functionalization logic in total synthesis
Gutekunst, W. R., & Baran, P. S. (2011) · Chemical Society Reviews · doi:10.1039/c0cs00182a · Cited by 1,399
Rho, K. S., Jeong, L., Lee, G., Seo, B.-M., Park, Y. J., Hong, S.-D., Roh, S., Cho, J. J., Park, W. H., & Min, B.-M. (2006) · Biomaterials · doi:10.1016/j.biomaterials.2005.08.004 · Cited by 876
Metadata
- Authors
- Motiwala, H. F., Armaly, A. M., Cacioppo, J. G., Coombs, T. C., Koehn, K. R. K., Norwood, V. M., & Aubé, J.
- Venue
- Chemical Reviews
- Publisher
- American Chemical Society (ACS)
- Published
- 2022-07-17
- Volume
- 122
- Issue
- 15
- Pages
- 12544-12747
- ISSN
- 0009-2665 (ISSN-L)
- 1520-6890
- OpenAlex
- W4285677181
- Cited by
- 593
- References
- 180
- FWCI
- 8.99
- Type
- journal article
- Language
- en
- Open access
- closed
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- Motiwala, H. F., Armaly, A. M., Cacioppo, J. G., Coombs, T. C., Koehn, K. R. K., Norwood, V. M., & Aubé, J. (2022). HFIP in Organic Synthesis. Chemical Reviews. https://doi.org/10.1021/acs.chemrev.1c00749
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