Mechanistically guided workflow for relating complex reactive site topologies to catalyst performance in C–H functionalization reactions

RC Cammarota, W Liu, J Bacsa… - Journal of the …, 2022 - ACS Publications
Leveraging congested catalyst scaffolds has emerged as a key strategy for altering innate
substrate site-selectivity profiles in C–H functionalization reactions. Similar to enzyme active …

[HTML][HTML] Using IR vibrations to quantitatively describe and predict site-selectivity in multivariate Rh-catalyzed C–H functionalization

EN Bess, DM Guptill, HML Davies, MS Sigman - Chemical science, 2015 - pubs.rsc.org
Achieving selective C–H functionalization is a significant challenge that requires
discrimination between many similar C–H bonds. Yet, reaction systems employing Rh2 …

Deconvoluting Nonlinear Catalyst–Substrate Effects in the Intramolecular Dirhodium-Catalyzed C–H Insertion of Donor/Donor Carbenes Using Data Science Tools

LW Souza, BR Miller, RC Cammarota, A Lo… - ACS …, 2023 - ACS Publications
Interactions between catalysts and substrates can be highly complex and dynamic, often
complicating the development of models to either predict or understand such processes. A …

Correlating reactivity and selectivity to cyclopentadienyl ligand properties in Rh (III)-catalyzed C–H activation reactions: an experimental and computational study

T Piou, F Romanov-Michailidis… - Journal of the …, 2017 - ACS Publications
CpXRh (III)-catalyzed C–H functionalization reactions are a proven method for the efficient
assembly of small molecules. However, rationalization of the effects of cyclopentadienyl …

Key selectivity controlling elements in rhodium-catalyzed C–H functionalization with donor/acceptor carbenes

Z Ren, DG Musaev, HML Davies - ACS Catalysis, 2022 - ACS Publications
Computational studies on the dirhodium (tetracarboxylate)-catalyzed C–H functionalization
with donor/acceptor carbenes reveal that the enantioselectivity and site-selectivity of this …

[HTML][HTML] Multitask prediction of site selectivity in aromatic C–H functionalization reactions

TJ Struble, CW Coley, KF Jensen - Reaction Chemistry & Engineering, 2020 - pubs.rsc.org
Aromatic C–H functionalization reactions are an important part of the synthetic chemistry
toolbox. Accurate prediction of site selectivity can be crucial for prioritizing target compounds …

Leveraging Regio- and Stereoselective C(sp3)–H Functionalization of Silyl Ethers to Train a Logistic Regression Classification Model for Predicting Site-Selectivity …

YT Boni, RC Cammarota, K Liao… - Journal of the …, 2022 - ACS Publications
The C–H functionalization of silyl ethers via carbene-induced C–H insertion represents an
efficient synthetic disconnection strategy. In this work, site-and stereoselective C (sp3)–H …

Enantioselective intermolecular C–H functionalization of primary benzylic C–H bonds using ((aryl)(diazo) methyl) phosphonates

Y Naeem, BT Matsuo, HML Davies - ACS catalysis, 2023 - ACS Publications
Catalyst-controlled C–H functionalization using donor/acceptor carbenes has been shown to
be an efficient process capable of high levels of site control and stereocontrol. This study …

Predictive Model for the [Rh2(esp)2]-Catalyzed Intermolecular C(sp3)–H Bond Insertion of β-Carbonyl Ester Carbenes: Interplay between Theory and Experiment

BD McLarney, S Hanna, DG Musaev, S France - ACS Catalysis, 2019 - ACS Publications
Intermolecular C (sp3)–H insertions of β-carbonyl ester dirhodium-carbenes are extremely
rare. Toward developing efficient reactions of these carbenes, a model for their insertion into …

Running Wild through Dirhodium Tetracarboxylate-Catalyzed Combined CH (C)-Functionalization/Cope Rearrangement Landscapes: Does Post-Transition-State …

W Guo, DJ Tantillo - Journal of the American Chemical Society, 2024 - ACS Publications
A special type of C–H functionalization can be achieved through C–H insertion combined
with Cope rearrangement (CHCR) in the presence of dirhodium catalysts. This type of …