Issue 10, 2019

Pd-catalyzed dearomative arylborylation of indoles

Abstract

A palladium-catalyzed dearomative arylborylation of indoles is reported, which provides straightforward access to structurally diverse indolines bearing vicinal tetrasubstituted and borylated trisubstituted stereocenters in moderate to good yields with excellent diastereoselectivities. By using a BINOL-based chiral phosphoramidite ligand and an sp2–sp3 mixed-boron reagent, an enantioselective dearomative arylborylation was achieved and chiral boron-containing products were accessed in up to 94% ee. Synthetic tranformations of the resulting organoborons were conducted to afford a number of unique indoline derivatives.

Graphical abstract: Pd-catalyzed dearomative arylborylation of indoles

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Dec 2018
Accepted
23 Jan 2019
First published
25 Jan 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3118-3122

Pd-catalyzed dearomative arylborylation of indoles

C. Shen, N. Zeidan, Q. Wu, C. B. J. Breuers, R. Liu, Y. Jia and M. Lautens, Chem. Sci., 2019, 10, 3118 DOI: 10.1039/C8SC05737K

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