Method for preparing alkyl borate compound based on iron catalysis

Abstract

The invention relates to a method for preparing an alkyl borate compound based on iron catalysis. The alkyl borate compound has a structural formula I shown in the specification, and is obtained by taking an aromatic olefin compound and bis(pinacolato)diboron as raw materials to react in the presence of a proton source under the action of an iron catalyst and alkali.

Description

technical field [0001] The invention relates to a method for preparing alkyl borate compounds based on iron catalysis. Background technique [0002] Alkylboronic esters and alkylboronic acids are a class of very important intermediates in the field of organic synthesis (Boronic Acids: Preparation and Applications in OrganicSynthesis and Medicine, Wiley-VCH, Weinheim, 2005), in various drugs, polymer materials, The synthesis of liquid crystal materials and fluorescent probe materials has been widely used. Due to its important value in the field of organic synthesis, it is particularly important to be able to easily and conveniently synthesize alkyl borate compounds with diverse functional groups. At present, the representative methods of synthesizing alkyl borate compounds mainly include: [0003] (1) Organic lithium reagents or organic Grignard reagents react with borates to generate alkylboronic acids or alkylboronic acid ester compounds (Organometallics 1983,2,1316.). Thi...

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Problems solved by technology

[0003] (1) Organic lithium reagents or organic Grignard reagents react with borates to generate alkylboronic acids or alkylboronic acid ester compounds (Organometallics 1983,2,1316.). This type of method was reported earlier, but the method uses organic Lithium reagents or organic Grignard reagents have high requirements for reaction operations, and the method has narrow adaptability to the functional groups of the substrates

[0004] (2) In recent years, most reports on the synthesis of alkyl borate compounds have been catalyzed by transition metals, and borylation reactions have been realized for alkyl compounds or halogenated hydrocarbons. Using this method, rhodium catalyzed alkyl compounds have been successfully realized. borylation reaction (Science 2000,287,1995.) and copper-catalyzed borylation reaction of halogenated hydrocarbons (Angew.Chem.Int.Ed.2012,51,528.), but such reactions often require harsher reaction conditions or add additional organic ligands

[0005] (3) At present, the most reported method is to use transition metals to catalyze the reaction of olefins with pinacolborane (Pinacolborane) or bis(pinacolato)diboron), and the transition metals used are mostly noble metals such as Rhodium (J.Am.Chem.Soc.2004,126,9200.), ruthenium (Organometallics 2007,26,1191.), etc., in order to reduce costs, the catalyst metal is changed to cheap transition metals such as copper (J.Am. There are more and more reports on Chem.Soc.2009,131,3160.), cobalt (J.Am.Chem.Soc.2013,135,19107.), but the use of these cheap transition metals often requires the addition of expensive , organic ligands that are difficult to synthesize, or complexes that need to be synthesized to obtain the corresponding metals as catalysts

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