Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes

Arao, Takafumi; Kondo, Kazuhiro; Aoyama, Toyohiko

doi:10.1016/j.tetlet.2007.04.025

Cited by 70 publications

(16 citation statements)

References 19 publications

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“…Kulasegaram and Kulawiec20a,b have disclosed studies on palladium‐catalyzed epoxide isomerization that lend support to this proposal 20c–e. 21 Subsequent nickel‐catalyzed 1,2‐arylation with boronic acids, a transformation demonstrated recently by the research groups of Itami and Aoyama,22a,b would deliver the observed product 22c–g. While the rearrangement and arylation reactions are known separately, a simple catalyst capable of effecting both elementary steps has not been identified.…”

Section: Optimization Studies For the Coupling Of P‐tol Styrene Oxidementioning

confidence: 99%

Nickel‐Catalyzed Cross‐Coupling of Styrenyl Epoxides with Boronic Acids

Nielsen¹,

Doyle²

2011

Angewandte Chemie

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Auf zur Mehrfachkatalyse: Ein Ni0‐Biaryldialkylmonophosphan‐Katalysator vermittelt die Titelreaktion (siehe Schema). Die röntgenographische Charakterisierung eines katalytisch aktiven Nickel‐Ligand‐Komplexes spricht für eine Redoxreaktion unter C sp 3‐O‐Bindungsaktivierung. Eine Vielzahl α‐substituierter Alkohole wurde effizient durch eine Folge mehrerer katalytischer Prozesse erhalten.

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Section: Optimization Studies For the Coupling Of P‐tol Styrene Oxidementioning

confidence: 99%

Nickel‐Catalyzed Cross‐Coupling of Styrenyl Epoxides with Boronic Acids

Nielsen¹,

Doyle²

2011

Angewandte Chemie

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“…A similar effect of the boron reagent has also been reported in the nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes. 102 The formation of the tributenolide derivative 66a was observed when the excess of 19b was increased, or when the reaction was conducted in anhydrous solvent, using 1,4-dioxane (dried with molecular sieves). The subsequent investigation into the scope and limitations of the rhodium-catalyzed alkylative lactonization showed that the reaction of the -hydroxy-,-acetylenic ester bearing a tertiary propargylic group resulted in a reversal of the regioselectivity compared to that observed in the palladium-catalyzed process.…”

Section: Scheme 82mentioning

confidence: 99%

Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

et al. 2014

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“…The physical data were comparable to those reported. 6 (4-tert-Butylphenyl)(1-naphthyl)methanol (2n) Colorless oil.…”

Section: (+)-(Biphenyl-2-yl)phenylmethanol [(+)-2m]mentioning

confidence: 99%

“…Herein, we would like to report the development of an asymmetric nickel-catalyzed 1,2-addition of arylboron reagents to aromatic aldehydes. 6 Initially our studies focused on the determination of the conditions for Ni(cod) 2 -catalyzed phenylation using various phosphine ligands, phenylboronic acid, and triphenylboroxin. As can be seen in Table 1, the dramatic effect of the boron reagent and ligand was observed.…”

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confidence: 99%

Development of Asymmetric Nickel-Catalyzed Arylation of Aromatic Aldehydes with Arylboron Reagents

Yamamoto¹,

Tsurumi²,

Sakurai³

et al. 2008

Synthesis

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A s y m m e t r i c N i c k e l -C a t a l y z e d A r y l a t i o n Abstract: The development of the nickel-catalyzed 1,2-addition of triarylboroxins to aromatic aldehydes in the presence of a phosphine ligand is described. This development allowed the asymmetric nickel-catalyzed 1,2-addition of arylboron reagents to aromatic aldehydes. The enantioselectivity is synthetically acceptable (up to 81% ee) using 1-naphthaldehyde and 2-substituted aromatic aldehydes as substrates. The results have enantioselectivity comparable to the best results reported by us for the rhodium-catalyzed arylation of aromatic aldehydes.The asymmetric arylation of aromatic aldehydes is one of the most important C-C bond-forming reactions, because optically active diarylmethanols are important intermediates for the synthesis of biologically active compounds. 1 Among various arylmetal reagents used, arylboron reagents are desirable due to the recent demand for safe and sustainable organic synthesis, as their reagents are less toxic and they are air-stable. Miyaura's group has reported that rhodium(I) complexes catalyze the 1,2-addition of arylboronic acids to aldehydes giving the corresponding products with 41% ee. 2 Although, later attention focused on asymmetric arylation with the combination of a rhodium catalyst and an arylboronic acid, 3 our method, exhibiting up to 85% enantioselectivity, gave the best results. 3c,f Recently, Ohta and Ito, 4a our group, 4b and others 4c-e reported the use of a less expensive palladium catalyst for the 1,2-addition of arylboronic acids to aromatic aldehydes. However, our method using a palladium catalyst gave no enantioselectivity. From the viewpoint of cost and practical convenience, the use of a more economical and naturally abundant metal catalyst such as nickel, rather than rhodium or palladium, is desirable. 5 To date, only one successful example of the nickel-catalyzed arylation of aldehydes with arylboron reagents has been reported by Shirakawa. 5a However, according to Shirakawa's report, 5a in the presence of a phosphine ligand, the arylation does not proceed at all, hence the extension to an asymmetric version of the nickel-catalyzed arylation seemed to be very difficult. Herein, we would like to report the development of an asymmetric nickel-catalyzed 1,2-addition of arylboron reagents to aromatic aldehydes. 6Initially our studies focused on the determination of the conditions for Ni(cod) 2 -catalyzed phenylation using various phosphine ligands, phenylboronic acid, and triphenylboroxin. As can be seen in Table 1, the dramatic effect of the boron reagent and ligand was observed. When phenylboronic acid was used as the boron reagent, the results for phenylation were not promising ( Table 1, entries 1 and 2). Next, the use of triphenylboroxin as the boron reagent was examined. After intensive screening of ligands, we found that the chemical yield was brought to an acceptable level by using (±)-Et-Duphos (6b) (Table 1, entry 10). Very interestingly, other five-membered chelating ligands such a...

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Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes

Cited by 70 publications

References 19 publications

Nickel‐Catalyzed Cross‐Coupling of Styrenyl Epoxides with Boronic Acids

Nickel‐Catalyzed Cross‐Coupling of Styrenyl Epoxides with Boronic Acids

Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

Development of Asymmetric Nickel-Catalyzed Arylation of Aromatic Aldehydes with Arylboron Reagents

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