Issue 15, 2023

Palladium-catalyzed synthesis of 4-sila-4H-benzo[d][1,3]oxazines by intramolecular Hiyama coupling

Abstract

A palladium-catalyzed synthesis of 4-sila-4H-benzo[d][1,3]oxazines, silicon-switched analogs of biologically relevant 4H-benzo[d][1,3]oxazines, was developed by the intramolecular Hiyama coupling of 3-amido-2-(arylsilyl)aryl triflates. The present reaction is an unusual way of utilizing the Hiyama coupling, enabling the synthesis of value-added organosilanes as the main products. The intramolecular nature of transmetalation with inversion of the stereochemistry at the silicon center was revealed by the mechanistic investigation, and an asymmetric variant of this process was also demonstrated to give silicon-stereogenic 4-sila-4H-benzo[d][1,3]oxazines with relatively high enantioselectivity.

Graphical abstract: Palladium-catalyzed synthesis of 4-sila-4H-benzo[d][1,3]oxazines by intramolecular Hiyama coupling

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Nov 2022
Accepted
21 Mar 2023
First published
22 Mar 2023
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., 2023,14, 4114-4119

Palladium-catalyzed synthesis of 4-sila-4H-benzo[d][1,3]oxazines by intramolecular Hiyama coupling

D. Lee and R. Shintani, Chem. Sci., 2023, 14, 4114 DOI: 10.1039/D2SC06425A

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