Ni-Catalyzed 1,2-Alkyl Borylation and Silylation of Allenes En Route to [1,3]-Bis-Organometallic Reagents

Velasco-Rubio, Álvaro; Cong, Fei; Tian, Yubiao; Martin, Ruben

doi:10.1021/acs.orglett.3c03574

Org. Lett.

2023

DOI: 10.1021/acs.orglett.3c03574

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Ni-Catalyzed 1,2-Alkyl Borylation and Silylation of Allenes En Route to [1,3]-Bis-Organometallic Reagents

Álvaro Velasco-Rubio,

Fei Cong,

Yubiao Tian

et al.

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2024

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Synthesis of Unsymmetrical 3,3′-Dialkyloxindole Boronic Esters from 3-Alkylidene-2-oxindoles Enabled by Copper Catalysis

Mondal,

Chungath,

Krishnan

et al. 2024

J. Org. Chem.

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We describe a 1,2-alkylboration of 3-alkylidene-2-oxindoles with a diboron reagent and alkyl bromides and iodides enabled by copper/bisphosphine catalysis. This scalable alkylboration method provides facile access to 3,3′dialkyloxindole boronic esters featuring an all-carbon quaternary stereocenter and an increased F(sp 3 ) fraction. In addition to good functional group tolerance and prolific utilization of drug/pesticide-derived alkyl iodides, the conversion of the C− B bond to a C−C/C−X bond offers further opportunities for structural variation of 3,3′-dialkyloxindoles.3-Alkylidene-2-oxindoles are omnipresent in various natural products and featured in therapeutic agents, including marketed drugs [e.g., sunitinib (Figure 1)]. 1 Additionally, 3-Note pubs.acs.org/joc

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Synthesis of Unsymmetrical 3,3′-Dialkyloxindole Boronic Esters from 3-Alkylidene-2-oxindoles Enabled by Copper Catalysis

Mondal,

Chungath,

Krishnan

et al. 2024

J. Org. Chem.

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show abstract

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Ni-Catalyzed 1,2-Alkyl Borylation and Silylation of Allenes En Route to [1,3]-Bis-Organometallic Reagents

Cited by 1 publication

References 59 publications

Synthesis of Unsymmetrical 3,3′-Dialkyloxindole Boronic Esters from 3-Alkylidene-2-oxindoles Enabled by Copper Catalysis

Synthesis of Unsymmetrical 3,3′-Dialkyloxindole Boronic Esters from 3-Alkylidene-2-oxindoles Enabled by Copper Catalysis

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