Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts

Siddiki, S. M. A. Hakim; Touchy, Abeda S.; Kon, Kenichi; Shimizu, Ken‐ichi

doi:10.1002/chem.201505109

Cited by 35 publications

(25 citation statements)

References 48 publications

(33 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The selectivity for the vinyl sulfone product is unique. The previous report for such a reaction with Ru and Pt as catalyst delivered the Julia olefination product.…”

Section: C−c Bond Formationmentioning

confidence: 95%

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions

Waiba

Maji

2020

ChemCatChem

View full text Add to dashboard Cite

Acceptorless dehydrogenative coupling (ADC) has emerged as a powerful tool in the chemists’ arsenal for the construction of various carbon‐carbon and carbon‐heteroatom bonds. These protocols are highly atom economical and environmentally benign as they do not require pre‐functionalized starting material and produce only dihydrogen (and water) as the by‐product. This technique, coupled with Earths’ abundant and less toxic manganese catalysis, can prove to be a vital strategy for the generation of molecular complexity from simple starting materials. Manganese catalyzed DHC has been of growing interest, and various low‐ and high‐valent manganese catalysts have been developed. These catalysts were demonstrated to show excellent catalytic activity for the formation of carbon‐carbon, carbon‐heteroatom bonds, and cascade reactions. In this mini‐review, we would like to highlight the recent progress that has been made in manganese catalyzed ADC reactions.

show abstract

“…The selectivity for the vinyl sulfone product is unique. The previous report for such a reaction with Ru and Pt as catalyst delivered the Julia olefination product.…”

Section: C−c Bond Formationmentioning

confidence: 95%

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions

Waiba

Maji

2020

ChemCatChem

View full text Add to dashboard Cite

show abstract

“…(E)-1-(tert-Butyl)-4-(prop-1-en-1-yl)benzene (4d). 24 Eluent: petroleum ether. Colorless oil, 30.3 mg (86%).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…(E)-5-(Prop-1-en-1-yl)benzo [d][1,3]dioxole (4h). 24 Eluent: petroleum ether/ethyl acetate = 60:1. Colorless oil, 20.3 mg (62%).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Nickel-Catalyzed Alkylation or Reduction of Allylic Alcohols with Alkyl Grignard Reagents

Yang

Wang

2020

J. Org. Chem.

View full text Add to dashboard Cite

By choosing different phosphine ligands, nickel-catalyzed selective alkylation and reduction of allylic alcohols with alkyl Grignard reagents were performed. The reaction using Ni(dppe)Cl2 as the catalyst resulted in the cross-coupling of allylic alcohols with primary alkyl Grignard reagents and cyclopropylmagnesium bromide. The reaction catalyzed by the combination of Ni(PCy3)2Cl2 and dcype led to the reduction of allylic alcohols. Secondary alkyl Grignard reagents except cyclopropylmagnesium bromide always led to reduction of allylic alcohols using either Ni(dppe)Cl2 or Ni(PCy3)2Cl2/dcype as the catalyst. In the reductive reaction β-H-containing alkyl Grignard reagents were required.

show abstract

“…23 Spectral data in accordance to previously published data. 24 3-Ethenylphenol (3k). Using general procedure A, 3hydroxybenzaldehyde (123 mg, 1.01 mmol) and HNTf 2 (0.1 mL, 0.1 mol%) provided alkene 3k (108 mg, 0.89 mmol, 88%) as a colorless oil after purification by flash column chromatography (eluent: hexane:Et 2 O, 4:1).…”

Section: -Ethenylbenzonitrile (3i)mentioning

confidence: 99%