20651-65-4

Usage

Physical state at room temperature

Colorless clear liquid

Molecular weight

146.21 g/mol

Uses

Intermediate in chemical synthesis, production of pharmaceuticals, agrochemicals, and other industrial products

Safety precautions

Can be harmful if inhaled, swallowed, or in contact with skin

Handling

Proper personal protective equipment and handling procedures should be observed

InChI:InChI=1/C10H13F/c1-2-3-4-9-5-7-10(11)8-6-9/h5-8H,2-4H2,1H3

Upstream product

• 20651-67-6 4-butyliodobenzene 
• 109-72-8 n-butyllithium 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 4426-47-5 butylboronic acid 
• 1215100-19-8 4-n-butylphenyl trifluoromethanesulfonate 
• 2248-13-7 1-(but-3-en-1-yl)-4-fluorobenzene 
• 145240-28-4 4-butylphenylboronic acid 
• 1188303-84-5 2-(4-butylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1422263-65-7 C₁₅H₂₀BNO₄ 
• 1412414-09-5 potassium (4-n-butylphenyl)trifluoroborate 
• 625458-85-7 2-(4-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 693-04-9 butyl magnesium bromide 
• 109-65-9 1-bromo-butane 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 53179-12-7 Clopimozide 

Relevant academic research and scientific papers

Amido PNP pincer complexes of palladium(II) and platinum(II): Synthesis, structure, and reactivity

The synthesis of a series of divalent palladium and platinum complexes containing amido PNP pincer ligands of the type [N(o-C6H4PR2)2]? (R = Ph (1a), iPr (1b)) is reported. Metathetical reactions of [1a–b]PdCl or [1a–b]PtCl with a variety of alkyl Grignard reagents or LiHBEt3 in ethereal or arene solutions generate their corresponding alkyl or hydride complexes [1a]PdR1 (R1 = Me, Et, nBu), [1b]PdR1 (R1 = Me, Et, H), [1a]PtR1 (R1 = Me, Et, nBu, nHexyl, H), and [1b]PtR1 (R1 = Me, H). Although these organometallic complexes are all thermally stable, including those containing β-hydrogen atoms even at elevated temperatures, compounds [1a]PdH and [1b]PtR1 (R1 = Et, nBu, nHexyl) are not isolable due to facile decomposition. The stability and reactivity of these complexes are discussed. The chloro [1a]PdCl is a superior catalyst precursor to [1b]PdCl, [1a]PtCl, and [1b]PtCl in Kumada couplings, affording, for instance, n-butyl arenes nearly quantitatively. The X-ray structures of [1b]PtCl, [1b]PtMe, [1b]PdEt, [1a]PtnBu, [1b]PdH, and [1b]PtH are presented.

Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides

Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.

Spatially isolated palladium in porous organic polymers by direct knitting for versatile organic transformations

We report here a direct knitting Method for preparation of highly robust, effective while air- and moisture-tolerant, and readily recyclable three-dimensional (3D) porous polymer-Pd network (PPPd) from the widely used Pd(PPh3)4. Electro-beam induced Pd atom crystallization was observed for the first time in organic polymer and revealed the ultrafine dispersion of palladium atoms. Challenging types of Suzuki-Miyaura couplings, reductive coupling of aryl halides and oxidative coupling of arylboronic acid were successively catalyzed by PPPd in aqueous media. Also catalytically selective C–H functionalization reactions were achieved with orders of magnitude more efficient than conventional Pd homogeneous catalysts. The strategy developed here provides a practical method for easy-to-make yet highly efficient heterogeneous catalysis.

Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands

In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air.

A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is

Studying regioisomer formation in the pd-catalyzed fluorination of aryl triflates by deuterium labeling

Isotopic labeling has been used to determine that a portion of the desired product in the Pd-catalyzed fluorination of electron-rich, non-ortho-substituted aryl triflates results from direct C-F cross-coupling. In some cases, formation of a Pd-aryne intermediate is responsible for producing undesired regioisomers. The generation of the Pd-aryne intermediate occurs primarily via ortho-deprotonation of a L·Pd(Ar)OTf (L = biaryl monophosphine) species by CsF and thus competes directly with the transmetalation step of the catalytic cycle. Deuterium labeling studies were conducted with a variety of aryl triflates.

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

FLUORINATION OF ARYL COMPOUNDS

The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by a fluorine atom. The compositions include a metal ion source, a electrophilic fluorine source, a base, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluorine atom. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the electrophilic fluorine source is a source of 18F.

Pd-catalyzed nucleophilic fluorination of aryl bromides

On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.