Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant
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TLDR
A protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature is reported.Abstract:
Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature. This mild protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope. Notably, functionalization of (iso)quinolines, pyridines, phenanthrolines, quinazoline, and other heterocyclic compounds with unactivated primary, secondary, and tertiary alkyl halides proceeds smoothly under the standard conditions. The robustness of this protocol is further demonstrated by the late-stage functionalization of complex nitrogen-containing natural products and drugs.read more
Citations
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Recent Advances in Minisci-Type Reactions.
TL;DR: A review of the remarkably large body of literature that has appeared on this topic over the last decade in an attempt to provide guidance to the synthetic chemist, as well as a perspective on both the challenges that have been overcome and those that still remain.
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Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.
Stefano Crespi,Maurizio Fagnoni +1 more
TL;DR: This review summarizes the main alternative approaches for the generation of unstabilized alkyl radicals, using photons as traceless promoters, thus allowing a new era of photon democracy.
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Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds.
Rolando Cannalire,Sveva Pelliccia,Luca Sancineto,Ettore Novellino,Gian Cesare Tron,Mariateresa Giustiniano +5 more
TL;DR: In this paper, the authors present a review of the recent developments in the field of late stage functionalization of complex biorelevant compounds and highlight the expected future progress and potential applications.
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Beyond Friedel and Crafts: Directed Alkylation of C-H Bonds in Arenes.
Gwilherm Evano,Cédric Theunissen +1 more
TL;DR: Insightful alkylations of C-H bonds in (hetero)arenes will be overviewed comprehensively in this Review, in which electronic and steric properties, governed by the presence of one (or multiple) heteroatom(s), ensure high levels of regioselectivity.
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Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides.
TL;DR: This approach exploits the intri-guing photochemical activity of electron donor-acceptor (EDA) complexes between N-amidopyridinium salts and bromide, which provides a photoactive handle capable of generating silyl radicals and driving the alkylation process.
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