钯(II)催化的 C(sp3)-H 键羰基化反应：通向 1,4-二羰基化合物的新途径。
Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.
机构信息
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
J Am Chem Soc. 2010 Dec 15;132(49):17378-80. doi: 10.1021/ja108754f. Epub 2010 Nov 17.
Abstract
Pd(II)-catalyzed β-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.
摘要
Pd(II)催化的 N-芳酰胺β-C(sp(3))-H 羰基化反应在 CO（1 atm）条件下实现。酰胺导向的 C(sp(3))-H 断裂和 CO 插入到生成的[Pd(II)-C(sp(3))]键后，分子内的 C-N 还原消除得到相应的琥珀酰亚胺，它们可以很容易地转化为 1,4-二羰基化合物。该方法对于含有α-氢原子的底物是有效的，并且可以应用于环丙烷的亚甲基 C(sp(3))-H 羰基化。
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