Products Cited in Publications Worldwide Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines

Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines

Grace Trammel; Rositha Kuniyil; Phillip Crook; Peng Liu; M. Kevin Brown

DOI: PMID:

Abstract

Indole dearomatization is an important strategy to access indolines, a motif present in a variety of natural products and pharmaceuticals. Herein, a method for transition-metal catalyzed regiodivergent dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermolecular dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >50:1 rr and >20:1 dr) from readily available starting materials. Additionally, the origin of regiodivergence was explored experimentally and computationally to uncover the remarkable interplay between carbonyl orientation of the N-protecting group on indole, electronics of the C2-C3 p-bond, and sterics. The method enabled the first enantioselective synthesis of (-)-azamedicarpin.

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N-Boc-indole-2-boronic acid

A794095213318-44-698%

N-Boc-indole-2-boronic acid

100.0/25g

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