Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters
Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters
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DOI：
10.1021/jo1004907
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发表时间：
2010-06-04
影响因子：
3.6
通讯作者：
Hilt, Gerhard
中科院分区：
文献类型：
--
作者：
Auvinet, Anne-Laure;Harrity, Joseph P. A.;Hilt, Gerhard
室温钴催化的炔基硼酸酯与1，3-二烯的[4 + 2]环加成反应为合成苯基芳族硼酸酯提供了一种简便、通用的方法。探讨了两种互补的芳构化策略，包括原位消除和DDQ氧化，后者更具普遍性。最后，通过手性（外消旋）DMAP催化剂的合成，证明了该技术产生高度官能化联芳基的潜力。
The room-temperature cobalt-catalyzed [4 + 2] cycloaddition of alkynylboronates and 1,3-dienes provides a convenient and general method for the synthesis of benzene-based aromatic boronic esters. Two complementary aromatization strategies involving in situ elimination and DDQ oxidation were explored, with the latter finding more generality. Finally, the potential of this technique to generate highly functionalized biaryls has been demonstrated via the synthesis of chiral (racemic) DMAP catalysts.