Wu Xianqing, Wang Chenglong, Liu Ning, Qu Jingping, Chen Yifeng
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology 130 Meilong Road, Shanghai, China.
Nat Commun. 2023 Oct 31;14(1):6960. doi: 10.1038/s41467-023-42716-2.
Transition metal-catalyzed carbonylative reaction with CO gas are among the central task in organic synthesis, enabling the construction of highly valuable carbonyl compound. Here, we show an earth-abundant nickel-catalyzed three-component tandem acylzincation/cyclization sequence of allene and alkylzinc reagent with 1 atm of CO under mild conditions. This protocol is featured by broad functional group tolerance with high reaction selectivity, providing a rapid and convenient synthetic method for the construction of diverse fully substituted benzotropone derivatives. Mechanistic studies reveal that the installation of a cyano group tethered to allene moiety enables the high regio- and stereoselectivity of this acylzincation of allene, allowing the selective formation of three consecutive C-C bonds in a highly efficient manner.
过渡金属催化的与一氧化碳气体的羰基化反应是有机合成的核心任务之一，能够构建高价值的羰基化合物。在此，我们展示了一种以地球上储量丰富的镍为催化剂，在温和条件下，使丙二烯、烷基锌试剂与1个大气压的一氧化碳发生三组分串联酰锌化/环化反应序列。该方法具有广泛的官能团耐受性和高反应选择性，为构建各种全取代苯并环庚三烯酮衍生物提供了一种快速便捷的合成方法。机理研究表明，连接在丙二烯部分的氰基的引入使得丙二烯的这种酰锌化反应具有高区域和立体选择性，从而能够以高效方式选择性地形成三个连续的碳 - 碳键。
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