Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis.
Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis.
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DOI：
10.1021/acs.orglett.6b00911
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发表时间：
2016-06-03
期刊：
影响因子：
5.2
通讯作者：
Molander GA
中科院分区：
文献类型：
--
作者：
Karimi-Nami R;Tellis JC;Molander GA
通过应用光氧化还原/镍双重催化，实现了α-烷氧烷基和α-酰氧烷基三氟硼酸盐与芳基和杂芳基溴的不依赖保护基团的交叉偶联。反应在非常温和的条件下进行，具有出色的官能团相容性和优异的杂芳烃耐受性。该方法提供了对带有苄基、新戊酰基和N，N-二异丙基氨基甲酰基保护基团的受保护的仲苄醇基序的便利的获得。
Protecting-group-independent cross-coupling of α-alkoxyalkyl- and α-acyloxyalkyltrifluoroborates with aryl and heteroaryl bromides is achieved through application of photoredox/nickel dual catalysis. Reactions occur under exceptionally mild conditions, with outstanding functional group compatibility and excellent observed tolerance of heteroarenes. This method offers expedient access to protected secondary benzylic alcohol motifs bearing benzyl, pivaloyl, and N,N-diisopropylcarbamoyl protecting groups.