Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

被引：36

作者：

Lipp, Benjamin ^{[1
]}

Lipp, Alexander ^{[1
]}

Detert, Heiner ^{[1
]}

Opatz, Till ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 08期

关键词：

PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; RADICAL-ADDITION; FRAGMENTATION; CHEMISTRY; MECHANISM; CLEAVAGE; CATIONS; ACIDS; IONS;

D O I：

10.1021/acs.orglett.7b00652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A light-induced C-C-sigma-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp(3))-C(sp(3))-sigma-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield-radical cations which undergo a homolytic cleavage of a C(Sp(3))-C(sp(3))-sigma-bond rather than the well-known alpha-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.

引用

页码：2054 / 2057

页数：4

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