Skip to main content

Research Repository

Advanced Search

All Outputs (8)

A Domino Radical Amidation/Semipinacol Approach to All-Carbon Quaternary Centers Bearing an Aminomethyl Group (2023)
Journal Article
Dhak, M. S., Arunprasath, D., Argent, S. P., & Cuthbertson, J. D. (2023). A Domino Radical Amidation/Semipinacol Approach to All-Carbon Quaternary Centers Bearing an Aminomethyl Group. Chemistry - A European Journal, 29(47), Article e202300922. https://doi.org/10.1002/chem.202300922

A photoredox-mediated radical amidation ring-expansion sequence that enables the generation of all-carbon quaternary centers bearing a protected aminomethyl substituent is described. The methodology can be applied to both styrene and unactivated alke... Read More about A Domino Radical Amidation/Semipinacol Approach to All-Carbon Quaternary Centers Bearing an Aminomethyl Group.

Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan (2023)
Journal Article
Lee, J. C., Cuthbertson, J. D., & Mitchell, N. J. (2023). Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan. Organic Letters, 25(29), 5459-5464. https://doi.org/10.1021/acs.orglett.3c01795

Across eukaryotic proteomes, tryptophan is the least abundant of the 20 canonical amino acids, which makes it an ideal chemical handle for the late-stage functionalization of peptide and protein scaffolds with minimal production of undesired isoforms... Read More about Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan.

A Redox-Relay Heck Approach to Substituted Tetrahydrofurans (2023)
Journal Article
Byrne, T. J. M., Mylrea, M. E., & Cuthbertson, J. D. (2023). A Redox-Relay Heck Approach to Substituted Tetrahydrofurans. Organic Letters, 25(13), 2361-2365. https://doi.org/10.1021/acs.orglett.3c00769

An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly re... Read More about A Redox-Relay Heck Approach to Substituted Tetrahydrofurans.

Redox-neutral organocatalytic Mitsunobu reactions (2019)
Journal Article
Beddoe, R. H., Andrews, K. G., Magné, V., Cuthbertson, J. D., Saska, J., Shannon-Little, A. L., …Denton, R. M. (2019). Redox-neutral organocatalytic Mitsunobu reactions. Science, 365(6456), 910-914. https://doi.org/10.1126/science.aax3353

Nucleophilic substitution reactions of alcohols are amongst the most fundamental and strategically important transformations in organic chemistry. For over half a century these reactions have been achieved using stoichiometric, and often hazardous, r... Read More about Redox-neutral organocatalytic Mitsunobu reactions.

Palladium-catalyzed enantioselective C-H activation of aliphatic amines using chiral anionic BINOL-phosphoric acid ligands (2017)
Journal Article
Smalley, A. P., Cuthbertson, J. D., & Gaunt, M. J. (2017). Palladium-catalyzed enantioselective C-H activation of aliphatic amines using chiral anionic BINOL-phosphoric acid ligands. Journal of the American Chemical Society, 139(4), 1412-1415. https://doi.org/10.1021/jacs.6b12234

© 2017 American Chemical Society. The design of an enantioselective Pd(II)-catalyzed C-H amination reaction is described. The use of a chiral BINOL phosphoric acid ligand enables the conversion of readily available amines into synthetically valuable... Read More about Palladium-catalyzed enantioselective C-H activation of aliphatic amines using chiral anionic BINOL-phosphoric acid ligands.

Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles (2016)
Journal Article
Shaw, M. H., Shurtleff, V. W., Terrett, J. A., Cuthbertson, J. D., & MacMillan, D. W. (2016). Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles. Science, 352(6291), 1304-1308. https://doi.org/10.1126/science.aaf6635

The use of sp3 C–H bonds—which are ubiquitous in organic molecules—as latent nucleophile equivalents for transition metal–catalyzed cross-coupling reactions has the potential to substantially streamline synthetic efforts in organic chemistry while by... Read More about Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles.

Switching on elusive organometallic mechanisms with photoredox catalysis (2015)
Journal Article
Terrett, J. A., Cuthbertson, J., Shurtleff, V. W., & MacMillan, D. W. (2015). Switching on elusive organometallic mechanisms with photoredox catalysis. Nature, 524(7565), 330-334. doi:10.1038/nature14875

Transition-metal-catalysed cross-coupling reactions have become one of the most used carbon–carbon and carbon–heteroatom bond-forming reactions in chemical synthesis. Recently, nickel catalysis has been shown to participate in a wide variety of C−C b... Read More about Switching on elusive organometallic mechanisms with photoredox catalysis.

The direct arylation of allylic sp3 C–H bonds via organic and photoredox catalysis (2015)
Journal Article
Cuthbertson, J. D., & MacMillan, D. W. C. (2015). The direct arylation of allylic sp3 C–H bonds via organic and photoredox catalysis. Nature, 519(7541), 74-77. https://doi.org/10.1038/nature14255

The direct functionalization of unactivated sp3 C–H bonds is still one of the most challenging problems facing synthetic organic chemists. The appeal of such transformations derives from their capacity to facilitate the construction of complex organi... Read More about The direct arylation of allylic sp3 C–H bonds via organic and photoredox catalysis.