Direct regioselective C–H borylation of [5]helicene

R. P. Kaiser; J. Ulč; I. Císařová; D. Nečas

doi:10.1039/C7RA13021J

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Direct regioselective C–H borylation of [5]helicene†

R. P. Kaiser,

^a J. Ulč,

^a I. Císařová

^b and D. Nečas

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Faculty of Science, Charles University, Albertov 6, 12843 Praha 2, Czech Republic
E-mail: david.necas@natur.cuni.cz

^b Department of Inorganic Chemistry, Faculty of Science, Charles University, Albertov 6, 12843, Praha 2, Czech Republic

Abstract

Ir-catalyzed borylation of [5]helicene was studied for the first time. The obtained results indicate that borylation proceeded preferentially at the 2- and 3-positions. By using an appropriate catalytic system, 3-borylated [5]helicene can be formed as the major product in a high yield and regioselectivity (up to 89%, 8 : 1 ratio of isomers). The monoborylated [5]helicenes were further utilized in a Suzuki–Miyaura cross-coupling reaction to produce 2- or 3-arylated helicenes in very good isolated yields (80–94%).

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DOI: https://doi.org/10.1039/C7RA13021J
Article type: Paper
Submitted: 04 Dec 2017
Accepted: 16 Dec 2017
First published: 02 Jan 2018
This article is Open Access

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RSC Adv., 2018,8, 580-583

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Direct regioselective C–H borylation of [5]helicene

R. P. Kaiser, J. Ulč, I. Císařová and D. Nečas, RSC Adv., 2018, 8, 580 DOI: 10.1039/C7RA13021J

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Direct regioselective C–H borylation of [5]helicene†

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