Rhodium-catalyzed addition of arylboron compounds to nitriles, ketones, and imines

Ueura, Kenji; Miyamura, Sawako; Satoh, Tetsuya; Miura, Masahiro

doi:10.1016/j.jorganchem.2006.02.022

Cited by 111 publications

(26 citation statements)

References 31 publications

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“…Arylboronic acids and even arene CÀH bonds were successfully added to nitriles to generate various aryl ketones by the hydrolysis of the intermediate ketimine in trifluoroacetic acid. [7] Later, Lu and Zhao, [8] Miura et al, [9] and others [10] developed various catalytic systems for aryl ketone synthesis from nitriles and arylboronic acids, catalyzed by palladium or rhodium. Cheng et al developed a nickel-catalyzed addition of arylboronic acids to nitriles by using ZnCl 2 as the Lewis acid, under mild conditions.…”

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confidence: 99%

Direct Synthesis of Aryl Ketones by Palladium‐Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles

Liu

Zhou

Rao

et al. 2011

Chemistry A European J

119

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confidence: 99%

Direct Synthesis of Aryl Ketones by Palladium‐Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles

Liu

Zhou

Rao

et al. 2011

Chemistry A European J

119

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“…The stereochemical route in the Miyaura-Hayashi reaction mediated by Binap, as well as in the prodigious majority of metal-catalyzed stereoselective reactions, relies on the postulation that the substrates approach the metal so as to minimize the steric interactions with the expanded R groups of the chiral ligand structure. 160 Nevertheless, the half view of the Rh-disulfoxide complexes described above indicates that the system is barren of any remarkable steric hindrance around the metal center. In fact, the aryl groups on the sulfoxide moieties are directed away from the metal center and parallel to the atropisomeric scaffold, parting the oxygen atoms of the sulfoxide moieties as the only segments upcoming the metal center.…”

Section: Methodsmentioning

confidence: 98%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

106

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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“…[43] Although the reaction was initially optimized with phenylboronic acid, it was found to be easier with sodium tetraarylborates. [44] This method can be used to access a wide range of optically pure (or very nearly so) flavanones 34 . Electron-deficient sodium tetraarylborates afford the poorest yields (25% yield, 97% ee ) whereas more electron-rich substrates result in higher yields and enantioselectivities.…”

Section: Carbon–carbon Bond Formationmentioning

confidence: 99%

Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones

2011

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Flavanones, chromanones, and related structures are privileged natural products that display a wide variety of biological activities. Although flavanoids are abundant in nature, there are a limited number of available general and efficient synthetic methods for accessing molecules of this class in a stereoselective manner. Their structurally simple architectures belie the difficulties involved in installation and maintenance of the stereogenic configuration at the C2 position, which can be sensitive and can undergo epimerization under mildly acidic, basic, and thermal reaction conditions. This review presents the methods currently used to access these related structures. The synthetic methods include manipulation of the flavone/flavanone core, carbon-carbon bond formation, and carbon–heteroatom bond formation.

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Rhodium-catalyzed addition of arylboron compounds to nitriles, ketones, and imines

Cited by 111 publications

References 31 publications

Direct Synthesis of Aryl Ketones by Palladium‐Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles

Direct Synthesis of Aryl Ketones by Palladium‐Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones

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