Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids

Vasireddy, Purna Chandra Rao; Gogate, Akash R.; Enright, Dale R.; Smoliakova, Irina P.

doi:10.1016/j.poly.2021.115550

Polyhedron

2022

DOI: 10.1016/j.poly.2021.115550

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Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids

Purna Chandra Rao Vasireddy

Akash R. Gogate

Dale R. Enright

et al.

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Cited by 3 publications

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“…It is worth noting that the unexpected byproduct 2-phenylpyridine 1-oxide ( 7 ) was found when PPh 3 , dppe, or binap was used as ligand, which might be caused by the C–P bond activation of the corresponding ligand (Table , entries 5–8, and detailed information in SI). Furthermore, investigation of various bases (Table , entries 10–12) revealed that the C–C bond cleavage byproduct 5 was obtained when Cs 2 CO 3 was replaced by NaH or KO t Bu, which may be due to the protonation of intermediate in the reaction . Furthermore, the yield of 3b decreased when Cs 2 CO 3 was replaced by the relatively weak base K 2 CO 3 (Table , entry 12) .…”

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confidence: 99%

Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy

Long

et al. 2023

ACS Catal.

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Transition-metal-catalyzed C−C bond activation has emerged as an increasingly effective method for reorganizing a molecular skeleton. Ketone, as a versatile functional molecule, has been extensively studied for the C−C bond activation reaction. However, most C−C bond activation of unstrained ketones generally follows an oxidative addition strategy, while a nucleophilic 1,2-addition of a carbonyl moiety followed by β-C elimination strategy was less studied. Here a palladium-catalyzed C−C bond activation of an unstrained ketone enabled by a removable directing group through β-C elimination to synthesize 2-arylpyridine is described. The protocol features wide substrate scope with yields up to 95%, good functional group tolerance, and functionality of natural products. The 2-arylpyridine N-oxide products can be easily converted to the corresponding 2-arylpyridines under mild reaction conditions.

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mentioning

confidence: 99%

Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy

Long

et al. 2023

ACS Catal.

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Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

et al. 2022

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The transition-metal-catalyzed CÀ P bond cleavage has emerged as a powerful tool for the formation of both CÀ C and CÀ P bond. However, the transition-metal-catalyzed stereoselective cleavage of CÀ P bond is still undeveloped. Herein, we report a palladium-catalyzed stereoselective cleavage of CÀ P bond for the construction of P-stereogenic phosphines and stereogenic axis. This protocol enables the quick synthesis of atropisomers bearing a P-stereogenic center in high yields, diastereo-and enantioselectivities of up to 98 % ee, > 25 : 1 dr. The product is able to serve as chiral catalyst in phosphine catalyzed [3+2] cycloaddition of allenoates to imines, showing the great potential of the present methodology.

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Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

et al. 2022

View full text Add to dashboard Cite

The transition‐metal‐catalyzed C−P bond cleavage has emerged as a powerful tool for the formation of both C−C and C−P bond. However, the transition‐metal‐catalyzed stereoselective cleavage of C−P bond is still undeveloped. Herein, we report a palladium‐catalyzed stereoselective cleavage of C−P bond for the construction of P‐stereogenic phosphines and stereogenic axis. This protocol enables the quick synthesis of atropisomers bearing a P‐stereogenic center in high yields, diastereo‐ and enantioselectivities of up to 98 % ee, >25 : 1 dr. The product is able to serve as chiral catalyst in phosphine catalyzed [3+2] cycloaddition of allenoates to imines, showing the great potential of the present methodology.

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Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids

Cited by 3 publications

References 32 publications

Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy

Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy

Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

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