Selective decarbonylation via transition-metal-catalyzed carbon–carbon bond cleavage

H Lu, TY Yu, PF Xu, H Wei - Chemical Reviews, 2020 - ACS Publications
Transition-metal-catalyzed decarbonylation via carbon–carbon bond cleavage is an
essential synthetic methodology. Given the ubiquity of carbonyl compounds, the selective …

Synthetic Advantages of Defluorinative C− F Bond Functionalization

LV Hooker, JS Bandar - Angewandte Chemie, 2023 - Wiley Online Library
Much progress has been made in the development of methods to both create compounds
that contain C− F bonds and to functionalize C− F bonds. As such, C− F bonds are becoming …

Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides

CA Malapit, JR Bour, CE Brigham, MS Sanford - Nature, 2018 - nature.com
Abstract The Suzuki–Miyaura cross-coupling of organoboron nucleophiles with aryl halide
electrophiles is one of the most widely used carbon–carbon bond-forming reactions in …

Acyl Fluorides in Late‐Transition‐Metal Catalysis

Y Ogiwara, N Sakai - Angewandte Chemie International Edition, 2020 - Wiley Online Library
In this Review, we summarize the current state of the art in late‐transition‐metal‐catalyzed
reactions of acyl fluorides, covering both their synthesis and further transformations. In …

Mechanism and scope of nickel-catalyzed decarbonylative borylation of carboxylic acid fluorides

CA Malapit, JR Bour, SR Laursen… - Journal of the American …, 2019 - ACS Publications
This Article describes the development of a base-free, nickel-catalyzed decarbonylative
coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate …

Decarbonylative fluoroalkylation at palladium (II): from fundamental organometallic studies to catalysis

N Lalloo, CA Malapit, SM Taimoory… - Journal of the …, 2021 - ACS Publications
This Article describes the development of a decarbonylative Pd-catalyzed aryl–fluoroalkyl
bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [RFC (O) …

Acid Fluorides in Transition‐Metal Catalysis: A Good Balance between Stability and Reactivity

N Blanchard, V Bizet - Angewandte Chemie International …, 2019 - Wiley Online Library
Several recent reports outlined the singular reactivity of acid fluorides as excellent
electrophiles in transition‐metal catalysis. These species undergo oxidative addition of the …

Synthesis of N-CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3 Carbamoyl Fluorides

CDT Nielsen, FG Zivkovic… - Journal of the American …, 2021 - ACS Publications
The expansion of chemical space associated with ubiquitous motifs is key to unleash new
properties and functions. In this context, alkynamides, prevalent in numerous drugs and …

Direct access to acyl fluorides from carboxylic acids using a phosphine/fluoride deoxyfluorination reagent system

SB Munoz, H Dang, X Ispizua-Rodriguez… - Organic …, 2019 - ACS Publications
A fast and simple method for deoxyfluorination of carboxylic acids is presented. The protocol
employs commodity chemicals (PPh3, NBS, fluoride), affording products in excellent yields …

Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination

Y Liang, Z Zhao, A Taya, N Shibata - Organic Letters, 2021 - ACS Publications
We describe a novel reagent system to obtain acyl fluorides directly from three different
functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is …