1236076-70-2

Usage

Boronic acid derivative

The compound is derived from boronic acid, which is a key feature in its chemical properties and reactivity.

Unique structure

The compound has a distinctive structure that includes a cyclopropane ring and a boron atom, which contribute to its versatility in organic synthesis.

Building block

It is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and materials, due to its ability to form carbon-carbon bonds and its compatibility with different chemical reactions.

Suzuki-Miyaura cross-coupling reactions

The compound is employed in this type of reaction to form carbon-carbon bonds, which is an essential step in creating complex organic molecules.

Potential applications in catalysis

2-([1,1'-bi(cyclopropan)]-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can act as a ligand in metal-catalyzed reactions, making it a valuable component in the development of new catalytic processes.

Important roles in the development of new chemical compounds and materials

The compound's versatility and reactivity in various chemical reactions make it a crucial component in the creation of new molecules and materials for various applications.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 126689-01-8 cyclopropylboronic acid pinacol ester 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 60629-95-0 1-bromo-1-cyclopropylcyclopropane 

Downstream Products

• 1236076-54-2 1-(1-cyclopropylcyclopropyl)benzene 
• 1236076-56-4 2-(1-cyclopropylidene-2-methylethyl)-1,3,5-trimethylbenzene 
• 1236076-55-3 1,4-bis(1-cyclopropylcyclopropyl)benzene 
• 1236076-71-3 1-(1-cyclopropylcyclopropyl)-4-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents

α-Functionalization of alkyl boronic esters and homologation of aryl boronic esters by regioselective radical C(sp3)-H activation in boron-ate complexes is reported. Reaction of commercial or readily accessed aryl boronic acid pinacol esters with alkyl lithium reagents provides boron-ate complexes. Selective α-C-H abstraction by in situ generated trifluoromethyl radicals leads to radical anions that undergo electron transfer oxidation followed by 1,2-aryl/alkyl migration from boron to carbon to give the α-arylated/alkylated alkyl boronic esters. The valuable boronic ester functionality remains in the products and the cheap trifluoromethyl iodide acts as the oxidant in these C-C couplings. The 1,2-alkyl migration from boron to carbon is highly stereospecific allowing access to stereoisomerically pure boronic esters.

Convenient access to various 1-cyclopropylcyclopropane derivatives

1-Bromo-1-cyclopropylcyclopropane (1), which is easily accessible in two steps from methyl cyclopropanecarboxylate, does not form a stable Grignard reagent: upon reaction with elemental magnesium, yet it readily undergoes bromine/ lithium exchange without rearrangement upon treatment with tert-butyllithium in diethyl ether/pentane at -78 °C, and the resulting 1-lithio-1-cyclopropylcyclopropane can be trapped with various electrophiles to give the correspondingly 1-substituted bicyclopropyl derivatives 10 in yields ranging from 38 to over 90 % (13 examples). The (1-cyclopropylcyclopropyl) boronate 10m, which is also obtained from the 1-lithio derivative, has been subjected to Suzuki cross couplings with a number of aryl halides to furnish 1-aryl-1,1′bicyclopropyl compounds 11 (4 examples, 14-50% yield), predominantly without rearrangement. Further transformations of 1-cyclopropylcyclopropanecarbaldehyde (10e) have provided 2-(1- cyclopropylcyclopropyl)glycme (16), ethyl 3-(1-cyclopropylcyclopropyl)acrylate (17), and its cycloadducts with the nitrone 18 and cyclopentadiene 19, albeit the latter only in poor yield.