A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis

The Journal of Organic Chemistry
Anon BunritJoseph S M Samec

Abstract

An atom-efficient route to pyrroles substituted in the β-position has been achieved in four high yielding steps by a combination of Pd, Ru, and Fe catalysis with only water and ethene as side-products. The reaction is general and gives pyrroles substituted in the β-position with linear and branched alkyl, benzyl, or aryl groups in overall good yields. The synthetic route includes a Pd-catalyzed monoallylation step of amines with substituted allylic alcohols that proceeds to yield the monoallylated products in moderate to excellent yields. In a second step, unsymmetrical diallylated aromatic amines are generated from the reaction of a second allylic alcohol with high selectivity in moderate to good yields by control of the reaction temperature. Ru-catalyzed ring-closing metathesis performed on the diallylated aromatic amines yields the pyrrolines substituted in the β-position in excellent yields. By addition of ferric chloride to the reaction mixture, a selective aromatization to yield the corresponding pyrroles substituted in the β-position was achieved. A reaction mechanism involving a palladium hydride, generated from insertion of palladium to O-H of an allyl alcohol, that is responsible for the C-O bond cleavage to generate ...Continue Reading

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Citations

Aug 29, 2017·Chemistry, an Asian Journal·Zheng-Le ZhaoShu-Li You
Nov 28, 2017·Chemistry : a European Journal·Sunisa AkkarasamiyoJoseph S M Samec
Apr 17, 2019·The Journal of Organic Chemistry·Wenbo HuangYanlong Gu
Mar 9, 2018·The Journal of Organic Chemistry·Thanya RukkijakanJoseph S M Samec
Jun 23, 2020·The Journal of Organic Chemistry·Xiao-De AnJian Xiao
Aug 17, 2021·ACS Omega·Olatunji S Ojo, Alejandro Bugarin
Jun 11, 2020·The Journal of Organic Chemistry·Enrique Gil de MontesAntonio J Moreno-Vargas
Dec 3, 2020·The Journal of Organic Chemistry·Dan ChangGuo-Jun Deng

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