2012
DOI: 10.1021/ja300308c
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Hydrazone as the Directing Group for Ir-Catalyzed Arene Diborylations and Sequential Functionalizations

Abstract: The use of hemilabile pyridine-hydrazone N,N-ligands allows the highly selective Ir-catalyzed ortho,ortho'-directed diborylation of aromatic N,N-dimethylhydrazones in near-quantitative yields. One-pot sequential Suzuki-Miyaura cross-coupling with different aryl bromides provides a short entry to unsymmetrically substituted 2,6-diarylbenzaldehyde derivatives.

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Cited by 140 publications
(96 citation statements)
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References 29 publications
(16 reference statements)
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“…[5] An example of the latter class is Hartwig’s use of silylhydrides to facilitate the borylation ortho to OH and NH functionality and effect the functionalization at sp 2 positions in arylsilanes. [5a, 5c] Likewise, Lassaletta has shown that conversion of aryl aldehydes to hydrazones facilitates ortho -boyrlations. [5e] Nevertheless, these methods require installation and removal of the directing group.…”
mentioning
confidence: 99%
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“…[5] An example of the latter class is Hartwig’s use of silylhydrides to facilitate the borylation ortho to OH and NH functionality and effect the functionalization at sp 2 positions in arylsilanes. [5a, 5c] Likewise, Lassaletta has shown that conversion of aryl aldehydes to hydrazones facilitates ortho -boyrlations. [5e] Nevertheless, these methods require installation and removal of the directing group.…”
mentioning
confidence: 99%
“…[5a, 5c] Likewise, Lassaletta has shown that conversion of aryl aldehydes to hydrazones facilitates ortho -boyrlations. [5e] Nevertheless, these methods require installation and removal of the directing group.…”
mentioning
confidence: 99%
“…[7] Around the same time, several other research groups, including those of Sawamura, [8] Lassaletta [9] and Hartwig, [10] also reported similar borylation reactions involving functionalized arenes. The selectivity of these reactions has been attributed to the formation of an interaction between the coordinating heteroatom in the carbonyl group and the iridium metal center.…”
Section: Introductionmentioning
confidence: 96%
“…The selectivity of these reactions has been attributed to the formation of an interaction between the coordinating heteroatom in the carbonyl group and the iridium metal center. [7][8][9] Herein, we describe the development of a new process for the vinylic C-H borylation of cyclic 1 and acyclic α,β-unsaturated esters 3 with 2, using an in-situ-generated iridium complex consisting of readily available [Ir(X)(cod)]2 (X = OMe or Cl) and AsPh3 as a catalyst with octane as a solvent. [11] This reaction proceeded chemoselectively at 80 or 120 °C to give the corresponding alkenylboronic compounds 4 or 5 in high yields (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%
“…[16] Secondly, the sequencing of the ortho C À H olefination and scission of the pyrazolidinone ring was probed. Subjecting hydrazone [17] 8 to conditions A with ethyl acrylate only afforded slight decomposition, which indicates that the CÀH olefination should occur prior to any opening of the pyrazolidinone ring (Scheme 3 a). To study the sequencing of the 2nd olefination and the scission of the pyrazolidinone ring, an isolated sample of 3 aa was subjected to conditions B (benzyl acrylate), but no reaction occurred.…”
mentioning
confidence: 99%