Accessing Elaborated 2,1-Borazaronaphthalene Cores Using Photoredox/Nickel Dual-Catalytic Functionalization

被引：42

作者：

Jouffroy, Matthieu ^{[1
]}

Davies, Geraint H. M. ^{[1
]}

Molander, Gary A. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 07期

关键词：

SINGLE-ELECTRON TRANSMETALATION; VISIBLE-LIGHT; MERGING PHOTOREDOX; NICKEL CATALYSIS; CROSS-COUPLINGS; DRUG DISCOVERY; B-N; HALIDES; ALKYLSILICATES; OXIDATION;

D O I：

10.1021/acs.orglett.6b00466

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly effective method for derivatizing 2,1-borazaronaphthalene cores using ammonium alkylbis-(catecholato)silicates via photoredox/nickel dual catalysis is reported. By forging C-sp(3)-C-sp(2) bonds via this approach, alkyl fragments with various functional groups can be introduced to the azaborine core, affording previously inaccessible heterocyclic isosteres in good to excellent yields. The base-free, room-temperature conditions outlined allow sensitive functional group tolerance, even permitting the cross-coupling of unprotected primary and secondary amines.

引用

页码：1606 / 1609

页数：4

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