Kleinmans, Roman published the artcilePhotoredox-enabled 1,2-dialkylation of α-substituted acrylates via Ireland-Claisen rearrangement, Safety of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Chemical Science (2021), 12(8), 2816-2822, database is CAplus and MEDLINE.
The 1,2-dialkylation of simple feedstock acrylates RC(=CH2)C(O)OR1 [R = H, Me, F, i-Pr, naphthalen-1-yl, etc.; R1 = prop-2-en-1-yl, 4-ethenyloxan-4-yl, 2-chloroprop-2-en-1-yl, 2-(4-oxocyclohexylidene)ethyl, etc.] for the synthesis of valuable tertiary carboxylic acids R2CH2C(R)(R3)C(O)OH [R2 = cyclohexyl, oxan-4-yl, 5-(2,5-dimethylphenoxy)-2-methylpentan-2-yl, etc.; R3 = prop-2-en-1-yl, 2-(oxan-4-ylidene)ethyl, 2-chloroprop-2-en-1-yl, etc.] by merging Giese-type radical addition with an Ireland-Claisen rearrangement have been reported. Key to success is the utilization of the reductive radical-polar crossover concept under photocatalytic reaction conditions to force the [3,3]-sigmatropic rearrangement after alkyl radical addition to allyl acrylates. Using readily available alkyl boronic acids as radical progenitors, this redox-neutral, transition-metal-free protocol allows the mild formation of two C(sp3)-C(sp3) bonds, thus providing rapid access to complex tertiary carboxylic acids in a single step. Moreover, this strategy enables the efficient synthesis of highly attractive α,α-dialkylated γ-amino butyric acids (GABAs) R4(CH2)2C(CH3)(CH2CH=CH2)C(O)OH [R4 = dibutylaminyl, morpholin-4-yl, 4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl, etc.] when α-silyl amines R4CH2Si(CH3)3 are used as radical precursors – a structural motif that was still inaccessible in related transformations. Depending on the nature of the radical precursors and their inherent oxidation potentials, either a photoredox-induced radical chain or a solely photoredox mechanism is proposed to be operative.
Chemical Science published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Safety of 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
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