One-Pot Reaction of (β-Amino-α,α-difluoroethyl)phosphonates with Trifluoromethylated Ketones via Aza-Wittig Reagents

被引：11

作者：

Wang, Qian ^{[1
]}

Liu, Jiang ^{[1
]}

Wang, Nana ^{[1
]}

Pajkert, Romana ^{[2
]}

Mei, Haibo ^{[1
]}

Roschenthaler, Gerd-Volker ^{[2
]}

Han, Jianlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Coll Chem Engn, Nanjing 210037, Peoples R China

[2] Jacobs Univ Bremen gGmbH, Dept Life Sci & Chem, Campus Ring 1, D-28759 Bremen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Difluoro diazoalkanes; Aza-Wittig reaction; alpha-Fluorovinylphosphonates; C-F bond cleavage; Azoalkenes; IN-SITU GENERATION; FLUORINATED PHOSPHONATES; CATALYZED SYNTHESIS; DIAZOALKANES; FLUOROVINYLPHOSPHONATES; PHOSPHATES; PRODRUGS; ANALOGS;

D O I：

10.1002/adsc.202200330

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report a one-pot reaction of (beta-amino-alpha,alpha-difluoroethyl)phosphonates involving aza-Wittig reagents, in which, difluoromethylphosphonate-containing diazo and trifluoromethylated ketones assemble to furnish azo-containing alpha-fluorovinylphosphonates. Mechanism studies disclose a pathway, which contains an aza-Wittig reaction, water addition to hydrazone, and C-F bond cleavage with an aza-Wittig reagent as a key intermediate. This reaction is conducted at 60 degrees C affording a series of alpha-fluorovinylphosphonate compounds in 42-94% yields and Z-stereoselectivity. This work opens a vision for the difluoroalkyl-substituted diazos, and provides a strategy for the synthesis of alpha-fluorovinylphosphonate derivatives.

引用

页码：1969 / 1974

页数：6

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