![5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure](https://static.chemtradehub.com/structs/125/1256819-54-1-8620.webp "5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure")
Platinum(ii)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols
Literature Information
Publication Date
2019-07-17
DOI
10.1039/C9QO00831D
Impact Factor
5.281
Authors
Hidemasa Hikawa, Yuuki Matsuura, Shoko Kikkawa, Isao Azumaya
View Original
Abstract
A synthetic strategy for the water-promoted direct dehydrative coupling of indoles with benzyl alcohols catalyzed by PtCl2(PhCN)2 in 1,2-dichloroethane has been developed. Water molecules significantly accelerate C–C bond formation, whereas the reaction proceeds slowly under anhydrous conditions. Comparative rate plots for reactions in the presence of H2O and D2O show a kinetic solvent isotope effect (KSIE) of 1.5. A Hammett study of the dehydrative reaction of para-substituted benzhydrols shows negative ρ values, indicating a build-up of cationic charge during the rate-determining sp3 C–O bond cleavage step. Our catalytic system can be used on the gram scale with simplified product isolation and catalysis is performed using 1 mol% of a Pt(II) catalyst with an additional molecule of water.
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Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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lohepta[1,2-a]naphthalen-5-one structure](https://static.chemtradehub.com/structs/538/53800-21-8-9f18.webp "(3R,4aR,7aS,9aR,10S,11R,13aR,13bS,15aS,15bR)-3,11-Dihydroxy-10-(hydroxymethyl)-4,4,7a,10,13a,15b-hexamethyl-1,2,3,4,4a,7,7a,8,9,9a,10,11,12,13,13a,13b,14,15,15a,15b-icosahydro-5H-naphtho[2',1':4,5]cyc
lohepta[1,2-a]naphthalen-5-one structure")
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