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Usage

Uses

Used in Chemical Synthesis:
POTASSIUM OCTYLTRIFLUOROBORATE is used as a reactant for the preparation of boronic acids and esters through hydrolysis with silica gel and water. This application is crucial in the synthesis of various organic compounds and pharmaceuticals.
Used in Suzuki-Miyaura Cross-Coupling:
In the field of organic chemistry, POTASSIUM OCTYLTRIFLUOROBORATE is used as a reactant for Suzuki-Miyaura cross-coupling reactions. This reaction is an essential method for forming carbon-carbon bonds, which are vital in the synthesis of complex organic molecules and pharmaceuticals.
Used in Palladium-Catalyzed Suzuki-Miyaura-Type Cross-Coupling Reactions:
POTASSIUM OCTYLTRIFLUOROBORATE is also used as a reactant in palladium-catalyzed Suzuki-Miyaura-type cross-coupling reactions with alkenyl bromides. This application is significant in the synthesis of conjugated dienes and other complex organic structures.
Used in Hydrodeboration Reactions:
Furthermore, POTASSIUM OCTYLTRIFLUOROBORATE is utilized as a reactant in hydrodeboration reactions. These reactions are important for the synthesis of various organic compounds, particularly those containing boron atoms, which have applications in materials science and pharmaceuticals.

Upstream product

• 1279123-63-5 potassium hydrogenfluoride 
• 121-43-7 Trimethyl borate 
• 17049-49-9 octylmagnesium bromide 
• 28741-08-4 n-octylboronic acid 
• 111-83-1 1-bromo-octane 
• 66217-56-9 4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane 
• 629-27-6 1-Iodooctane 
• 111-66-0 oct-1-ene 

Downstream Products

• 28741-08-4 n-octylboronic acid 
• 109093-06-3 5-n-octyl-8-hydroxyquinoline 
• 111-87-5 octanol 

Relevant academic research and scientific papers

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

One-Step Synthesis of Acylboron Compounds via Copper-Catalyzed Carbonylative Borylation of Alkyl Halides**

A copper-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.

Total Synthesis of Waltherione F, a Nonrutaceous 3-Methoxy-4-quinolone, Isolated from Waltheria indica L. F.

Waltherione F was totally synthesized in seven steps and 31% overall yield from 2-nitro-3-methylanisole without the use of protecting groups. Key steps in the sequence were a Suzuki-Miyaura coupling to attach the n-octyl chain and a microwave-promoted cyclization of an acetonyl anthranilate to give the heterocyclic core whose 3-OH was O-methylated.

5-Alkyl-8-hydroxyquinolines: Synthesis and Application in Dye-Sensitized Solar Cells

The use of co-adsorbents in dye-sensitized solar cells (DSCs) increases both the power-conversion efficiency and long-term stability of these devices. Co-adsorbents usually consist of a hydrophobic moiety attached on a carboxylic or phosphoric acid terminal anchoring group, which chemisorbs on the semiconductor surface. In this work, the synthesis of a new family of 8-quinolinol derivatives bearing alkyl chains of variable length at the 5-position is described and their comparative efficiency as effective bidentate co-adsorbents in DSCs is evaluated. The key step towards their straightforward modular synthesis is a Suzuki coupling between 5-chloro-8-methoxyquinoline and alkyltrifluoroborates. The new compounds showed better performance as co-adsorbents in terms of cell efficiency as compared to their alkylcarboxylic acid analogues, with the best results obtained from the derivative bearing the longer dodecyl alkyl chain.

Preparation of alkylmagnesium reagents from alkenes through hydroboration and boron-magnesium exchange

Tolerant: Alkylmagnesium reagents can be synthesized from alkenes through a sequence of hydroboration and subsequent boron-magnesium exchange using a method that tolerates different functional groups (see scheme). The resulting alkylmagnesium reagents can be used in carbon-carbon bond forming reactions, such as alkylation reactions or transition-metal-catalyzed cross-coupling reactions. Copyright

Oxidative nucleophilic substitution: Transformation of alkylboronic derivatives

An efficient amidation reaction is described in this paper. Potassium alkyltrifluoroborate salts can be transforming to amides from nitriles in the presence of copper acetate and boron trifluoride. An extension of this reaction allowed the formation of amines, ethers, and C-C bond.

The reactivity of potassium polyfluoroaryl-, polyfluoroalkenyl-, and perfluoroalkyltrifluoroborates and their hydrocarbon analogues towards acids of different strength: A systematic study of the hydrodeboration

The hydrodeboration of the (fluoroorgano)trifluoroborates K [RFBF3] [RF = C6F5, XCF=CF (X - F, cis- and trans-Cl, -C3F7O, cis-C2F5, trans-C4F9, -C4H9) and C6F13]and of the organotrifluoroborates K [RBF3] (R = C6H5, cis- and trans-C4H9CH=CH, C4H9 and C8H17) with CH3CO2H (100%), CF3CO2H (100 %), aqueous HF and anhydrous HF was investigated. In the alkenyltrifluoroborates K [R′=CFCFBF3] the formal replacement of BF3 by a proton occurred stereospecifically under retention of the configuration. The 19F NMR spectra of K [RFBF3] in acids indicate strong interactions of the BF3 group with protons or acid molecules.

Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates.

[figure: see text] The palladium-catalyzed coupling reaction of potassium alkyltrifluoroborates with aryl- or alkenyltriflates proceeds to afford the corresponding arenes or alkenes in high yield. The borates are all solids, stable in air, and thus can be stored on the shelf indefinitely. The cross coupling can be effected using PdCl2(dppf).CH2Cl2 as the catalyst in THF-H2O in the presence of Cs2CO3. A variety of functional groups can be tolerated within the borate and/or the triflate coupling partner.