HFIP in organic synthesis

HF Motiwala, AM Armaly, JG Cacioppo… - Chemical …, 2022 - ACS Publications
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 …

Nitrene transfer catalysts for enantioselective C–N bond formation

M Ju, JM Schomaker - Nature Reviews Chemistry, 2021 - nature.com
Abstract Transition-metal-catalysed, non-enzymatic transformations of C–H and C= C bonds
to C–N bonds through nitrene transfer (NT) are powerful synthetic tools to prepare valuable …

Bifunctional sulfilimines enable synthesis of multiple N-heterocycles from alkenes

Q Cheng, Z Bai, S Tewari, T Ritter - Nature Chemistry, 2022 - nature.com
Intramolecular cyclization of nitrogen-containing molecules onto pendant alkenes is an
efficient strategy for the construction of N-heterocycles, which are of paramount importance …

Selective 1, 2‐Aminoisothiocyanation of 1, 3‐Dienes Under Visible‐Light Photoredox Catalysis

W Guo, Q Wang, J Zhu - Angewandte Chemie International …, 2021 - Wiley Online Library
Abstract Selective three‐component 1, 2‐diamination of 1, 3‐dienes with concurrent
introduction of two orthogonally protected amino groups remains unknown despite its …

Copper-catalyzed three-component aminofluorination of alkenes and 1, 3-dienes: direct entry to diverse β-fluoroalkylamines

G Feng, CK Ku, J Zhao, Q Wang - Journal of the American …, 2022 - ACS Publications
Rapid and efficient access to structurally diverse β-fluoroalkylamines is in high demand, with
their wide presence and great importance in medicinal chemistry and drug development …

Divergent Synthesis of CF3‐Substituted Allenyl Nitriles by Ligand‐Controlled Radical 1,2‐ and 1,4‐Addition to 1,3‐Enynes

F Wang, D Wang, Y Zhou, L Liang, R Lu… - Angewandte Chemie …, 2018 - Wiley Online Library
A ligand‐controlled system that enables regioselective trifluoromethylcyanation of 1, 3‐
enynes has been identified, which provides access to a variety of CF3‐containing tri‐and …

The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines

VCM Gasser, S Makai, B Morandi - Chemical Communications, 2022 - pubs.rsc.org
Electrophilic aminating reagents have seen a renaissance in recent years as effective
nitrogen sources for the synthesis of unprotected amino functionalities. Based on their …

A Combined Spectroscopic and Computational Study on the Mechanism of Iron-Catalyzed Aminofunctionalization of Olefins Using Hydroxylamine Derived N–O …

S Chatterjee, I Harden, G Bistoni… - Journal of the …, 2022 - ACS Publications
Herein, we study the mechanism of iron-catalyzed direct synthesis of unprotected
aminoethers from olefins by a hydroxyl amine derived reagent using a wide range of …

Hydrogen bonding phase-transfer catalysis with potassium fluoride: enantioselective synthesis of β-fluoroamines

G Pupo, AC Vicini, DMH Ascough, F Ibba… - Journal of the …, 2019 - ACS Publications
Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle
and low-cost. However, poor solubility in organic solvents coupled with limited strategies to …

Catalytic diastereo-and enantioselective fluoroamination of alkenes

KM Mennie, SM Banik, EC Reichert… - Journal of the …, 2018 - ACS Publications
The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-
catalyzed fluorination of allylic amines is reported. The method employs HF–pyridine as a …