Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.
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DOI:
10.1021/ja508317j
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发表时间:
2014-10-01
影响因子:
15
通讯作者:
Tunge, Jon A.
Tunge, Jon A.
中科院分区:
化学1区
文献类型:
--
作者:
Lang, Simon B.;O'Nele, Kathryn M.;Tunge, Jon A.

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采用光氧化还原和钯催化相结合的方法促进了顽固性α-氨基和苯乙酸烯丙基酯的室温脱羧烯丙基化。这个操作简单的过程产生二氧化碳作为唯一的副产品,并提供直接访问烯化烷烃。经过光化学氧化后,羧酸盐进行自由基脱羧,产生位点特异性的自由基中间体,并进行烯丙基化。提出了一种自由基双催化机理。利用类似的反应条件也对游离苯乙酸进行了烯化反应。
A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions.
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