Tetraorganoindates as Nucleophilic Coupling Partners in Pd-Catalyzed Cross-Coupling Reactions

Lee, Phil Ho; Lee, Sung Wook; Seomoon, Dong

doi:10.1021/ol035883o

Cited by 86 publications

(17 citation statements)

References 51 publications

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“…In 2003, the Lee group reported a Pd-catalyzed cross-coupling of aryl halides, triflates, benzyl bromides and acid chlorides with tetraorganoindate complexes 432. The tetraorganoindates were prepared in situ by the reaction of indium trichloride and alkyl, aryl or alkenyl lithium or magnesium bromides.…”

Section: Cross-coupling With Alkylindium Reagentsmentioning

confidence: 99%

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

2011

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Introduction 1418 1.1. List of Common Ligands 1419 2. Alkylzinc Reagents 1419 2.1. Synthesis of Alkylzinc Reagents 1419 2.2. Stability of Alkylzinc Reagents 1420 2.3. Cross-Coupling Reactions of Alkylzinc Reagents 1421 2.4. Palladium-Catalyzed Cross-Coupling Reactions of Alkylzinc Reagents 1423 2.4.1. Palladium-Catalyzed C(sp 2 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1423 2.4.2. Palladium-Catalyzed C(sp 3 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1427 2.4.3. Palladium-Catalyzed C(sp)-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1428 2.4.4. Formation of Ketones via Palladium-Catalyzed Negishi Coupling with Alkylzinc Reagents 1429 2.5. Nickel-Catalyzed Cross-Coupling Reactions of Alkylzinc Reagents 1429 2.5.1. Nickel-Catalyzed C(sp 2 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1429 2.5.2. Nickel-Catalyzed Carboxylations with Alkylzinc Reagents 1430 2.5.3. Nickel-Catalyzed C(sp 3 )--(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1430 2.5.4. Mechanistic Insights in Nickel-Catalyzed Cross-Couplings 1433 3.

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Section: Cross-coupling With Alkylindium Reagentsmentioning

confidence: 99%

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

2011

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“…Purification by FC on silica gel (pentane:EtOAc: 20:1) afforded a slightly yellow oil (5.4 g, 69%). The physical data are in agreement with those reported in the literature: 1 H NMR (CDCl 3 , 300 MHz): δ 7.78 (d, J = 7.0 Hz 2 H), 7.42–7.27 (m, 3 H), 6.99 (dd, J = 17.1, 10.6 Hz, 1 H), 6.26 (d, J = 17.1, H), 5.75 (d, J = 10.6, H) 19…”

Section: Methodsmentioning

confidence: 99%

Controlled nitroxide‐mediated radical polymerization of methyl and phenyl vinyl ketone

Hepperle

Luftmann

Studer

2012

J. Polym. Sci. A Polym. Chem.

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The article describes unprecedented nitroxide‐mediated radical polymerization of methyl and phenyl vinyl ketone (MVK and PVK) using a sterically highly hindered alkoxyamine as initiator/regulator. It is shown that controlled polymerization of PVK is far more difficult to achieve than controlled MVK polymerization. Whereas for MVK high conversion resulting in polyvinyl ketone with low polydispersity index is readily obtained, the PVK polymerization provides good results only in the presence of free nitroxide and styrene as additives. Vinyl ketone polymerizations are analyzed by ESI mass spectrometry. These MS studies provide insights into the problems associated with the controlled nitroxide‐mediated polymerization of PVK. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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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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Tetraorganoindates as Nucleophilic Coupling Partners in Pd-Catalyzed Cross-Coupling Reactions

Cited by 86 publications

References 51 publications

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Controlled nitroxide‐mediated radical polymerization of methyl and phenyl vinyl ketone

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

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