Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

被引：8

作者：

Zhang, Kena ^{[1
]}

Provot, Olivier ^{[1
]}

Alami, Mouad ^{[1
]}

Tran, Christine ^{[1
]}

Hamze, Abdallah ^{[1
]}

机构：

[1] Univ Paris Saclay, BioCIS, CNRS, F-92290 Chatenay Malabry, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 02期

关键词：

ISOCOMBRETASTATIN A-4; BIOLOGICAL EVALUATION; PALLADIUM; REAGENTS; HYDRAZONES; OLEFINS; HECK; 1,1-DIARYLETHYLENES; SULFONYLHYDRAZONES; DIARYLMETHANES;

D O I：

10.1021/acs.joc.1c02580

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study shows that various di-and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consisted of PdCl2(CH3CN)(2)/dppp, LiOtBu as a base, and cyclopentyl methyl ether as a green solvent. In addition, we performed a gram-scale transformation using NTH derivatives and benzylic phosphates having a C sp(2)-Cl bond. The latter was used as a starting point for further postfunctionalization of the key intermediates.

引用

页码：1249 / 1261

页数：13

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