Nickel(0) Triethyl Phosphite Complex-Catalyzed Allylic Substitution with Retention of Regio- and Stereochemistry

Yatsumonji, Yasutaka; Ishida, Yoshito; Tsubouchi, and Akira; Takeda, Takeshi

doi:10.1021/ol702122d

Cited by 89 publications

(32 citation statements)

References 19 publications

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“…Most nickel-catalyzed protocols require high catalyst loadings and long reaction times [ 59 , 60 , 61 , 62 , 63 , 64 , 65 ]. Recently, it was shown that strongly coordinating NHC-ligands can allow a more efficient reaction to occur (Equation 9) [ 66 ].…”

Section: Nickel-catalyzed Arylation Of Thiolsmentioning

confidence: 99%

Transition Metal Catalyzed Synthesis of Aryl Sulfides

2011

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The presence of aryl sulfides in biologically active compounds has resulted in the development of new methods to form carbon-sulfur bonds. The synthesis of aryl sulfides via metal catalysis has significantly increased in recent years. Historically, thiolates and sulfides have been thought to plague catalyst activity in the presence of transition metals. Indeed, strong coordination of thiolates and thioethers to transition metals can often hinder catalytic activity; however, various catalysts are able to withstand catalyst deactivation and form aryl carbon-sulfur bonds in high-yielding transformations. This review discusses the metal-catalyzed arylation of thiols and the use of disulfides as metal-thiolate precursors for the formation of C-S bonds.

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Section: Nickel-catalyzed Arylation Of Thiolsmentioning

confidence: 99%

Transition Metal Catalyzed Synthesis of Aryl Sulfides

2011

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“…In this context, allylic halides, carbonates, and carboxylates are utilized as the most convenient substrates, and their reactionm echanismsi nvolve as imple nucleophilic attack to the p-allyl metal species.W eh ave focused on both fundamental and practical research of Ni-based catalysts because of their anomalous activities towardavariety of transformationst o replacep recious metal catalysts with cheap and abundant metals. [2,3] Ni-catalyzed allylic substitution reactions with soft nucleophiles such as amines, [4] alcohols, [5] and thiols [5] are not so welld eveloped;i nf act, nickel is ar ather hard metal and thus its complexes favorably catalyzea llylic substitution reactions with hard nucleophiles such as Grignardr eagents, [6] organoboron, [7] organotin, [8] and organozinc [9] compounds.…”

Section: Introductionmentioning

confidence: 99%

Pentacoordinated Carboxylate π‐Allyl Nickel Complexes as Key Intermediates for the Ni‐Catalyzed Direct Amination of Allylic Alcohols

Kita

Sakaguchi

Hoshimoto

et al. 2015

Chemistry A European J

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Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2 ] and 1,1'-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4 NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4 NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η(3) -allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.

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“…[1] Several transition metals including palladium, [2] molybdenum, [3] iridium, [4] rhodium, [5] tungsten, [6] nickel, [7] iron [8] and ruthenium, [9] which exhibit different specificities in terms of regioselectivity properties, have been used for this purpose. In this context, the regioselectivity control is of crucial importance when unsymmetrical allylic derivatives are involved.…”

Section: Introductionmentioning

confidence: 99%

Benzylic Imidazolidinium, 3,4,5,6‐Tetrahydropyrimidinium and Benzimidazolium Salts: Applications in Ruthenium‐Catalyzed Allylic Substitution Reactions

et al. 2008

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Imidazolidinium, tetrahydropyrimidinium and benzimidazolium salts were prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce ruthenium catalysts that are active for the substitution of allylic substrates by dimethyl malonate as a carbonucleophile and phenol. The influences of the N‐heterocyclic structures, as well as that of the benzylic N‐substituents, on the reactivity and regioselectivity were examined.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Nickel(0) Triethyl Phosphite Complex-Catalyzed Allylic Substitution with Retention of Regio- and Stereochemistry

Cited by 89 publications

References 19 publications

Transition Metal Catalyzed Synthesis of Aryl Sulfides

Transition Metal Catalyzed Synthesis of Aryl Sulfides

Pentacoordinated Carboxylate π‐Allyl Nickel Complexes as Key Intermediates for the Ni‐Catalyzed Direct Amination of Allylic Alcohols

Benzylic Imidazolidinium, 3,4,5,6‐Tetrahydropyrimidinium and Benzimidazolium Salts: Applications in Ruthenium‐Catalyzed Allylic Substitution Reactions

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