2018
DOI: 10.1021/acscatal.8b02928
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Cu-Catalyzed Decarboxylative Borylation

Abstract: A simple method for the conversion of carboxylic acids to boronic esters via redox-active esters (RAEs) is reported using copper catalysis. The scope of this transformation is broad, and compared with the known protocols available, it represents the most inexpensive, rapid, and operationally simple option. In addition to a full exploration of the scope, a kinetic study was performed to elucidate substrate and reagent concentration dependences.

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Cited by 144 publications
(81 citation statements)
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“…tert ‐Butyl 3‐((4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)methyl)azetidine‐1‐carboxylate (15g) . Yield: 40.4 g (90 %) from 44.6 g of tert ‐butyl 3‐((4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)methylene)azetidine‐1‐carboxylate ( 3g ); colourless oil.…”
Section: Methodsmentioning
confidence: 99%
“…tert ‐Butyl 3‐((4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)methyl)azetidine‐1‐carboxylate (15g) . Yield: 40.4 g (90 %) from 44.6 g of tert ‐butyl 3‐((4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)methylene)azetidine‐1‐carboxylate ( 3g ); colourless oil.…”
Section: Methodsmentioning
confidence: 99%
“…The reaction conditions reported are mild, the reactions are fast, and they tolerate a wide variety of functional groups leading to the Bpin-containing products in moderate yields. By contrast, substrates bearing halides were low yielding due to unavoidable protodehalogenation or alternative borylation processes [144].…”
Section: Borylation Of C-x Bondsmentioning
confidence: 99%
“…The products were analyzed by an HPLC system (LUMTECH) equipped with a C18 column and UV detector. The conversion of CAL and the selectivity to the products were calculated with Equation (3) and Equation (4): Conversion (%) = (1 -mol of residual CAL mol of initial CAL ) × 100 (3) Selectivity (M, %) = ( mol of product (M) mol of reacted CAL compound ) × 100 (4) After each reaction run, the catalyst was separated from the mixture by centrifugation, washed with ethanol several times, and then dried overnight.…”
Section: Catalytic Testsmentioning
confidence: 99%
“…[1] However, selective hydrogenation of C=O bond is not thermodynamically and kinetically favored. [2][3][4] Previous works indicate that noble metal displays slightly higher selective for the unsaturated alcohol. [1,[5][6][7][8][9] Nevertheless, the composites of noble metal have a higher performance than single noble metal due to the special interaction between them.…”
Section: Introductionmentioning
confidence: 99%