Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O–H Activation and Lewis Acid-Catalyzed Fluoride Shuttling

Moon, Hye Won; Lavagnino, Marissa N.; Lim, Soohyun; Palkowitz, Maximilian D.; Mandler, Michael D.; Beutner, Gregory L.; Drance, Myles J.; Lipshultz, Jeffrey M.; Scola, Paul M.; Radosevich, Alexander T.

doi:10.1021/jacs.3c08373

Cited by 6 publications

(4 citation statements)

References 108 publications

(57 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…185 Compound 56 was recently shown to be capable of the deoxyfluorination of primary, secondary, and tertiary alcohols when used in combination with a triarylborane as a fluoride shuttle. 186…”

Section: Compounds With a Group 15 Central Elementmentioning

confidence: 99%

Ligand-enforced geometric constraints and associated reactivity in p-block compounds

Hannah,

Chitnis

2024

Chem. Soc. Rev.

View full text Add to dashboard Cite

show abstract

Section: Compounds With a Group 15 Central Elementmentioning

confidence: 99%

Ligand-enforced geometric constraints and associated reactivity in p-block compounds

Hannah,

Chitnis

2024

Chem. Soc. Rev.

View full text Add to dashboard Cite

show abstract

“…In traditional studies of synthetic methodologies, extensive experiments have to be carried out, and the products are identified by spectroscopy. For the inverse design task, , researchers would often test hundreds or even thousands of combinations of reaction conditions and catalysts to identify an optimal solution because of the large while sparsely explored landscape. Numerous criteria must be satisfied in the process of chemical reaction design, encompassing factors such as mild operating temperatures, reasonable reaction durations, selectivity, and environmental friendliness.…”

Section: Introductionmentioning

confidence: 99%

Exploring Chemical Reaction Space with Machine Learning Models: Representation and Feature Perspective

Ding,

Qiang,

Chen

et al. 2024

J. Chem. Inf. Model.

View full text Add to dashboard Cite

Chemical reactions serve as foundational building blocks for organic chemistry and drug design. In the era of large AI models, data-driven approaches have emerged to innovate the design of novel reactions, optimize existing ones for higher yields, and discover new pathways for synthesizing chemical structures comprehensively. To effectively address these challenges with machine learning models, it is imperative to derive robust and informative representations or engage in feature engineering using extensive data sets of reactions. This work aims to provide a comprehensive review of established reaction featurization approaches, offering insights into the selection of representations and the design of features for a wide array of tasks. The advantages and limitations of employing SMILES, molecular fingerprints, molecular graphs, and physics-based properties are meticulously elaborated. Solutions to bridge the gap between different representations will also be critically evaluated. Additionally, we introduce a new frontier in chemical reaction pretraining, holding promise as an innovative yet unexplored avenue.

show abstract

“…Although these precedents have been triumphantly implemented, the C–C cross-coupling has been dominantly investigated, especially for the arylation and carboxylation of alcohols. However, the carbon–heteroatom bond construction from non-π-extended alcohols (nonallylic/propargylic alcohols) has been less explored . For instance, C–SS bond formation directly from alcohols is still unknown, whereas the structure of their products is difficult to realize by classic nucleophilic substitution reactions.…”

Section: Introductionmentioning

confidence: 99%

Nickel-Catalyzed Deoxygenative Disulfuration of Alcohols to Access Unsymmetrical Disulfides

Chen,

Shao,

Deng

2024

ACS Catal.

View full text Add to dashboard Cite

Given the abundance of alcohol feedstocks and the significance of disulfides, we herein report a nickel-catalyzed direct deoxygenative disulfuration of alcohols with trisulfide dioxides to access a wide range of disulfide molecules without the cumbersome decoration of coupling partners. The use of readily available dicyclohexylcarbodiimide to form transient isoureas provides the activation of the high bond dissociation energy of the C−O bond, which facilitates the straightforward conversion of nonderivatized alcohols to forge a C−SS bond. Notably, this method obviates a preactivation multistep procedure and provides a catalytic turnover under exogenous ligand and base-free conditions, featuring a broad substrate scope and functional group compatibility. It thus offers a robust alternative to existing methods for the precise construction of versatile disulfide compounds from more abundant and commercially available substrates. The synthetic utility of the method was further showcased by successful gram-scale experiments and disulfuration of structurally complex pharmaceuticals.

show abstract

Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O–H Activation and Lewis Acid-Catalyzed Fluoride Shuttling

Cited by 6 publications

References 108 publications

Ligand-enforced geometric constraints and associated reactivity in p-block compounds

Ligand-enforced geometric constraints and associated reactivity in p-block compounds

Exploring Chemical Reaction Space with Machine Learning Models: Representation and Feature Perspective

Nickel-Catalyzed Deoxygenative Disulfuration of Alcohols to Access Unsymmetrical Disulfides

Contact Info

Product

Resources

About