Access to Chiral γ-Butenolides via Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes

Chemical Communications ◽

10.1039/d1cc02295d ◽

2021 ◽

Author(s):

Zhen-Yao Dai ◽

Pu-Sheng Wang ◽

Liu-zhu Gong

Keyword(s):

Functional Groups ◽

Palladium Catalysis ◽

Mild Conditions ◽

Palladium Catalyzed

Asymmetric allylic C-H alkylation of 1,4-pentadienes with α-angelica lactones has been developed by tri-axial phosphoramidite-palladium catalysis. This reaction can tolerate a range of functional groups under mild conditions, furnishing versatile...

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Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

Synlett ◽

10.1055/s-0039-1690850 ◽

2020 ◽

Vol 31 (09) ◽

pp. 903-906

Author(s):

Taoufik Rohand ◽

Sanae Sbi ◽

Victor Mkpenie ◽

Kiyoshi Tanemura

Keyword(s):

Functional Groups ◽

Acetyl Chloride ◽

Stille Coupling ◽

Mechanistic Studies ◽

Major Step ◽

Mild Conditions ◽

Synthetic Strategy ◽

Ligand Free ◽

Palladium Catalyzed ◽

Solvent Free Synthesis

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.

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Palladium-Catalyzed C–H Bond Monofluorination of 2-Arylbenzo[d]oxazinone Using Nitrate as Crucial Promoter

Synthesis ◽

10.1055/s-0037-1611700 ◽

2019 ◽

Vol 51 (07) ◽

pp. 1578-1584 ◽

Cited By ~ 21

Author(s):

Xu-Qin Li ◽

Huu-Manh Vu ◽

Fei-Wu Chen

Keyword(s):

Functional Groups ◽

Palladium Catalysis ◽

Environmentally Friendly ◽

Palladium Catalyzed ◽

Plausible Mechanism

Monofluorination of 2-arylbenzo[d]oxazinones with N-fluorobenzenesulfonimide (NFSI) was achieved by palladium catalysis in moderate to good yields. Promoted by nitrate, the reaction provides an economic and environmentally friendly strategy. The synthesis of monofluorinated 2-arylbenzo[d]oxazinones has good compatibility with many common functional groups. The plausible mechanism of this monofluorination is discussed.

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Palladium-Catalyzed Highly Regioselective ortho-Halogenation of 2-Pyridyl Sulfoxides

Synlett ◽

10.1055/s-0036-1588756 ◽

2017 ◽

Vol 28 (10) ◽

pp. 1232-1236 ◽

Cited By ~ 2

Author(s):

Meng Sun ◽

Jun-Long Zhao ◽

Xiang-Xiang Chen ◽

Hu Xie ◽

Jiang-Tao Ren ◽

...

Keyword(s):

Functional Groups ◽

Activation Pathway ◽

Mild Conditions ◽

Palladium Catalyzed

A palladium-catalyzed regioselective ortho-halogenation of 2-pyridyl sulfoxides via a C–H activation pathway has been reported. Under the conditions established, this reaction proceeded smoothly and could tolerate a variety of functional groups under mild conditions.

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A new palladium-catalyzed coupling reaction of vinylic and allylic triflates with pyrimidine nucleosides

Canadian Journal of Chemistry ◽

10.1139/v91-031 ◽

1991 ◽

Vol 69 (2) ◽

pp. 198-200 ◽

Cited By ~ 10

Author(s):

Mohamed Ezeldin Hassan

Keyword(s):

Key Words ◽

Palladium Catalysis ◽

Coupling Reaction ◽

Pyrimidine Nucleosides ◽

Mild Conditions ◽

Palladium Catalyzed ◽

High Yields

Vinylic trifluoromethane sulfonates (triflates) form palladium intermediates that react with pyrimidine nucleosides to produce C-5 alkyl substituted nucleosides after hydrogenation of the vinylic coupling products with hydrogen and Pd/C in methanol. The reaction, which is run under mild conditions, appears to be a general one since both mono- and disubstituted vinylic triflates, as well as the cyclic ones, gave high yields of the corresponding C-5 alkyl-substituted nucleoside. The reaction with allyl triflate requires the use of the 5-chloromercurinucleoside. Key words: nucleosides, triflates, palladium catalysis

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Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

Chemical Communications ◽

10.1039/d0cc07596e ◽

2021 ◽

Vol 57 (16) ◽

pp. 2021-2024

Author(s):

Zhi-Chao Qi ◽

Qin-Xin Lou ◽

Yuan Niu ◽

Shang-Dong Yang

Keyword(s):

Palladium Catalysis ◽

Palladium Catalyzed ◽

Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

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Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽

10.1055/a-1401-4486 ◽

2021 ◽

Author(s):

Zheng-Yang Gu ◽

Yang Wu ◽

Feng Jin ◽

Bao Xiaoguang ◽

Ji-Bao Xia

Keyword(s):

Carbon Monoxide ◽

Palladium Catalysis ◽

Computational Studies ◽

Organic Azides ◽

Reaction Proceeds ◽

Palladium Catalyzed ◽

Directing Group ◽

And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

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Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis

Synlett ◽

10.1055/a-1320-6946 ◽

2020 ◽

Author(s):

Shengqing Zhu ◽

Lingling Chu ◽

Xiaoliang Feng ◽

Lei Guo

Keyword(s):

Functional Groups ◽

Aryl Halides ◽

Nickel Catalysis ◽

Mild Conditions ◽

Dual Catalysis

AbstractA formal ethylene alkylarylation reaction with aryl halides and alkyl oxalates enabled by synergistic photoredox/nickel catalysis is reported. This protocol takes advantage of borates as a traceless activation group, achieving the formal ethylene difunctionalized products via a catalytic three-component 1,2-alkylarylation of vinyl borate followed by a base-assisted deborylation process. The mild conditions allow for excellent functional groups compatibility and broad substrate scope.

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