2012
DOI: 10.1002/anie.201206518
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Transition‐Metal‐Free Alkoxycarbonylation of Aryl Halides

Abstract: Transitions: The title reaction has been developed for the synthesis of a variety of tert-butyl benzoates by employing 1,10-phenanthroline as an additive. Various functional groups were tolerated and heteroaryl iodides were also suitable substrates. Preliminary mechanism studies were conducted and indicate the participation of radical intermediates.

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Cited by 133 publications
(58 citation statements)
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“…One-carbon homologation of aryl halides (e.g., 92) leading to esters (e.g., 93) has also been reported using a combination of t-BuOK and a bidentate nitrogen ligand (1,10-phenanthroline) (4). Relatively good yields of esters are obtained under high pressure of CO [63]. The proposed mechanism involves SET from the strong base to the aryl iodide 92, generating an aryl radical that is trapped by CO to furnish the acyl radical.…”
Section: Alkyl Halide Carbonylationmentioning
confidence: 99%
“…One-carbon homologation of aryl halides (e.g., 92) leading to esters (e.g., 93) has also been reported using a combination of t-BuOK and a bidentate nitrogen ligand (1,10-phenanthroline) (4). Relatively good yields of esters are obtained under high pressure of CO [63]. The proposed mechanism involves SET from the strong base to the aryl iodide 92, generating an aryl radical that is trapped by CO to furnish the acyl radical.…”
Section: Alkyl Halide Carbonylationmentioning
confidence: 99%
“…To exclude AuNP generation by reduction with the solvent upon irradiation, we ran an experiment in the absence of polymer 4 with light. [38] We currently disregard formation of polyacids by air oxidation of the acyl radicals to the corresponding peracids followed by reduction as suggested by Scaiano et al, [21] since AuNP formation has to be conducted under argon atmosphere (O 2 is detrimental to this process). Note that complete photocleavage of the HAK groups should occur in af ew minutes,i fone considers at riplet lifetime in the range of 0.37-13 ns and aq uantum yield of 0.29-0.67 depending on the substituents at the para position of aryl group.…”
Section: Methodsmentioning
confidence: 99%
“…The use of a flow process resulted more efficient, versatile and sustainable compared to batch. Moreover, this operationally simple procedure complements well with the already available strategies for the preparation of tert -butyl esters, avoiding the use of inflammable and explosive gaseous isobutylene [35], the use of harsh conditions [36], the use of peroxides [37], the use of toxic gas such as CO or transition metals [3842]. The flow process, for the direct C- tert -butoxycarbonylation of organolithiums, has been optimized in a green solvent such as 2-MeTHF by a precise control of the residence time, and without using cryogenic conditions (Scheme 6).…”
Section: Reviewmentioning
confidence: 99%