Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds

Tato, Rubén; Riveiros, Ricardo; Sestelo, José Pérez; Sarandeses, Luis A.

doi:10.1016/j.tet.2011.11.075

Cited by 15 publications

(9 citation statements)

References 60 publications

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“…350 It is noteworthy that alkyl zirconocene chloride is an ineffective reagent under the present reaction conditions, and the same was noticed in Rh(I)-catalyzed reactions with imines. [352][353][354][355] Since the transfer of the alkyl group from Zr to Rh is slower than the alkenyl group, 356 this 1,4-addition reaction of 1 is expected to involve the creation of alkenyl rhodium species via the transmetallation at the first stage. The overall process is illustrated in Scheme 195, in which the 1,4-adducts are obtained from a catalytic cycle as a Zr-enolate 403.…”

Section: Organozirconiumsmentioning

confidence: 99%

“…Furthermore, when chiral ligands are employed, the conjugate addition reaction proceeds to completion giving only moderate enantioselectivity (Scheme 206, Table 119). 354 The effect of MeOH in the reaction mixture was also studied by NMR spectroscopic analysis. In the addition of MeOH, the PhInCl 2 reagent gave the same results as before.…”

Section: Miscellaneousmentioning

confidence: 99%

“…355,356 Thus it is likely that the role of MeOH in the Rhcatalyzed conjugate addition reactions is connected with the creation of the catalytic species and/or the methanolysis of the oxoallyl rhodium enolate as an intermediate (Scheme 207). 354 …”

Section: Miscellaneousmentioning

confidence: 99%

See 2 more Smart Citations

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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Section: Organozirconiumsmentioning

confidence: 99%

Section: Miscellaneousmentioning

confidence: 99%

See 1 more Smart Citation

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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“…In these transformations the R 3 In reagents transfer one of the three organic groups, a reaction pattern that contrasts that of cross-cou- [ pling reactions with aryl or alkenyl halides in which all three groups are efficiently transferred. [9] Herein we report that triorganoindium reagents react with allylic halides under rhodium catalysis. Recently, we discovered that organoindium reagents can also be used in Rh-catalyzed conjugate additions to electron-deficient olefins.…”

Section: Introductionmentioning

confidence: 99%

Rhodium‐Catalyzed Allylic Substitution Reactions with Indium(III) Organometallics

et al. 2012

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A novel rhodium‐catalyzed allylic substitution reaction using indium organometallics is reported. Aryl‐ and heteroarylindium reagents reacted in THF at 80 °C with primary and secondary allyl halides and their derivatives under rhodium(I) catalysis to afford the α‐substituted products in good yields and with high regio‐ and stereoselectivity. The reaction takes place with substoichiometric amounts of the triorganoindium reagents, which demonstrates the efficiency of the indium–rhodium transmetallation process in carbon–carbon bond‐forming reactions.

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“…In this reaction, triorganoindium reagents (R 3 In) can efficiently couple with a variety of organic electrophiles under palladium catalysis with high atom economy [ 5 , 6 , 7 , 8 ]. The process can be extended to other organoindium reagents [ 9 , 10 , 11 , 12 , 13 ] and transition metals in catalysis [ 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

et al. 2018

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The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120 °C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position.

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Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds

Cited by 15 publications

References 60 publications

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

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

Rhodium‐Catalyzed Allylic Substitution Reactions with Indium(III) Organometallics

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

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