Electrophilic Substitution of the Pyrrole Ring

doi:10.1016/b978-0-12-389840-1.50009-7

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2024

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“… 13 In addition, the advantages of using pyrrolidines as synthetic equivalents to pyrroles lie in their orthogonal reactivity. While pyrroles are sensitive to acids, 14 oxidants, 15 and react with electrophiles through the carbon skeleton, 16 pyrrolidines do not. Therefore, a pyrrolidine may be more robust and able to be carried through a synthetic sequence for a pyrrole to be revealed at a later stage.…”

Section: Introductionmentioning

confidence: 99%

B(C₆F₅)₃-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles

Alvarez-Montoya,

Gillions,

Winfrey

et al. 2024

ACS Catal.

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Pyrroles are important N-heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but is an underdeveloped approach due to the sensitivity of pyrroles to the oxidative conditions required to achieve such a transformation. Herein, we report a catalytic approach that employs commercially available B(C 6 F 5 ) 3 in an operationally simple procedure that allows pyrrolidines to serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.

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