Scalable Preparation of 4,4-Disubstituted Six-Membered Cyclic Sulfones

Hugelshofer, Cedric L.; Bao, Jianming; Du, Juana; Ashley, Eric R.; Yu, Wei; Ji, Tao; Hu, Bin; Liu, Dejun; Rondla, Ramu; Karampuri, Srinivas; Sharma, Vishal B.; Ethiraj, K. S.; Lim, Yeon‐Hee

doi:10.1021/acs.orglett.0c04141

Cited by 9 publications

(1 citation statement)

References 30 publications

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“…In addition, bulky α-functionalized exocyclic or acyclic amines could be accessed via cross-coupling in good efficiency ( 20 and 21 , 64% and 51% yield). Furthermore, the use of tertiary redox-active esters enabled the formation of quaternary carbons, as represented in the acyclic tert -butyl moiety and a cyclic β-substituted pyrrolidine, as well as a medicinally important cyclic sulfone ( 22 to 24 , 47% to 63% yield) ( 41 ). For α-oxy esters, radicals generated adjacent to both phenoxy and methoxy substituents could participate in cross-coupling with respectable efficiency, providing a new entry to the synthesis of hindered ethers ( 25 and 26 , 50% and 68% yield).…”

mentioning

confidence: 99%

A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

Liu

Lavagnino

Gould

et al. 2021

Science

117

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Radical substitution Nucleophilic substitution is a venerable reaction in organic chemistry. Typically, an incoming ion delivers two electrons to a carbon center while a departing ion takes two electrons away with it. The one-electron analog, homolytic substitution, is more rarely used, in part because the incoming neutral radicals can self-couple instead of bonding to the intended target. Liu et al . report that an iron porphyrin catalyst can direct homolytic substitution between primary and tertiary carbon radicals by selectively activating the primary partners. —JSY

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mentioning

confidence: 99%

A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

Liu

Lavagnino

Gould

et al. 2021

Science

117

View full text Add to dashboard Cite

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Divinyl Sulfone

Lucchi¹,

Fabbri²,

Santoyo‐González³

et al. 2021

Encyclopedia of Reagents for Organic Synthesis

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Copper‐Catalyzed α‐Arylation of Nitroalkanes with (Hetero)aryl Bromides/Iodides

Huang,

Li,

et al. 2024

Angewandte Chemie

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α‐Aryl substituted nitroalkanes are valuable synthetic building blocks that can be easily converted into a‐aryl substituted aldehydes, ketones, carboxylic acids, as well as amines. Herein, an efficient Cu/oxalamide‐catalyzed coupling between nitroalkanes and (hetero)aryl halides (Br, I) was developed to direct access highly diverse α‐aryl substituted nitroalkanes. Compared with the current state of art, this protocol is more environmentally friendly and practical for synthetic chemists. This approach is characterized by a broad substrate scope on both nitroalkane part (primary nitroalkanes and nitromethane) and sp2 halide part ((hetero)aryl bromides/iodides and alkenyl bromides/iodides). The excellent functional group tolerance was observed, which would enable real world synthetic applications. More importantly, TON of current transformation reached to 3640, when some aryl iodides were used as coupling partners. This represents currently the highest catalyst turnover for transition‐metal catalyzed α‐arylation of nitroalkanes. Furthermore, the successful application in late‐stage modification of complex molecules and synthesis of a known retinoid X receptor (RXR) antagonist exemplified its synthetic potential.

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Scalable Preparation of 4,4-Disubstituted Six-Membered Cyclic Sulfones

Cited by 9 publications

References 30 publications

A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

Divinyl Sulfone

Copper‐Catalyzed α‐Arylation of Nitroalkanes with (Hetero)aryl Bromides/Iodides

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Scalable Preparation of 4,4-Disubstituted Six-Membered Cyclic Sulfones

Cited by 9 publications

References 30 publications

A biomimetic S H 2 cross-coupling mechanism for quaternary sp 3 -carbon formation

A biomimetic S H 2 cross-coupling mechanism for quaternary sp 3 -carbon formation

Divinyl Sulfone

Copper‐Catalyzed α‐Arylation of Nitroalkanes with (Hetero)aryl Bromides/Iodides

Contact Info

Product

Resources

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A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation

A biomimetic S _H 2 cross-coupling mechanism for quaternary sp ³ -carbon formation