Mechanochemical Simmons–Smith cyclopropanation<i>via</i>ball-milling-enabled activation of zinc(0)

Pontini, Lorenzo; Leitch, Jamie A.; Browne, Duncan L.

doi:10.1039/d3gc00649b

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2024

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Cited by 6 publications

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“…Additional references were cited within the Supporting Information. [20][21][22][23][24][25][26][27][28]…”

Section: Supporting Informationmentioning

confidence: 99%

Thiophane‐Catalyzed Umpolung of N‐Bromoimides for Dibromination of Olefins

Wang,

Niu,

2024

Eur J Org Chem

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A thiophane‐catalyzed dibromination of olefins using NBS as the sole bromine source has been developed, providing a low‐cost and mild methodology for preparing vicinally dibrominated compounds from electron‐neutral or ‐deficient alkenes. The mechanistic investigation showed that 2,3‐dihydrothiophene generated in situ from the reaction of thiophane with NBS was the actual catalyst, which reversed the polarity of NBS to yield bromide ion.

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“…Additional references were cited within the Supporting Information. [20][21][22][23][24][25][26][27][28]…”

Section: Supporting Informationmentioning

confidence: 99%

Thiophane‐Catalyzed Umpolung of N‐Bromoimides for Dibromination of Olefins

Wang,

Niu,

2024

Eur J Org Chem

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Mechanochemical Mitsunobu Reactions

Williams,

Adarve Cardona,

Bolm

2024

Adv Synth Catal

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A Mitsunobu process performed under neat grinding conditions, using a mixer mill, is reported. It proceeds in the absence of reaction solvent and in short reactions times (10 – 20 min). A broad substrate scope encompassing primary and secondary alcohols, as well as oxygen, nitrogen, sulfur, and carbon‐centered nucleophiles is demonstrated. Application to the functionalization of a selection of APIs is shown, also. The developed process is amenable to scale up on a planetary ball‐mill, yielding over 2 grams of product. Finally, a representative alcohol is inverted with excellent stereoselectivity.

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