Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Organoboron Reagents
Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Organoboron Reagents
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DOI：
10.1021/ol801844w
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发表时间：
2008-11-06
期刊：
影响因子：
5.2
通讯作者：
Murakami, Masahiro
中科院分区：
文献类型：
--
作者：
Miura, Tomoya;Toyoshima, Takeharu;Murakami, Masahiro
钯（0）/单膦催化剂促进2-（炔基）芳基异氰酸酯与有机硼试剂的环化反应以产生立体定向的3-亚烷基羟吲哚。炔基和异氰酸基与Pd（0）进行氧化环化，形成氧杂环戊二烯中间体。随后的金属转移和还原消除提供产品。
A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(0) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.