N-heterocyclic carbene-catalyzed fluorinated silyl-Reformatsky reaction of aldehydes with difluoro (trimethylsilyl) acetate

Wang Ying; Xing Fen; Gu Cheng-Zhi; Li Wen-Juan; He Lin; Dai Bin; Du Guang-Fen

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N-heterocyclic carbene-catalyzed fluorinated silyl-Reformatsky reaction of aldehydes with difluoro (trimethylsilyl) acetate

机译：用二氟（三甲基甲硅烷基）丙酸盐醛的N-杂环卡蛋烯催化氟化甲硅烷基重构醛反应

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摘要

N-Heterocyclic carbenes (NHCs) have been employed as highly efficient organocatalysts for fluorinated silyl-Reformatslcy reaction of carbonyl compounds. In the presence of 5-10 mol % NHC A, various aldehydes and 2,2,2 trifluoroacetophenone reacted with difluoro (trimethylsilyl) acetate to produce 13 hydroxy gem difluoro esters in 20-96% yields. (C) 2017 Elsevier Ltd. All rights reserved.

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来源
《Tetrahedron》 |2017年第30期|共7页
作者
Wang Ying; Xing Fen; Gu Cheng-Zhi; Li Wen-Juan; He Lin; Dai Bin; Du Guang-Fen;
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作者单位

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

Shihezi Univ Sch Chem &

Chem Engn Key Lab Green Proc Chem Engn Xinjiang Bingtuan Shihezi 832000 Xinjiang Uygur Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
N-Heterocyclic carbene; Difluoro (trimethylsilyl) acetate; beta-hydroxy gem-difluoro ester; Silyl-Reformatsky reaction;

机译：N-杂环甲苯;二氟（三甲基甲硅烷基）乙酸盐;β-羟基宝石酯;甲硅烷基重新转化反应;

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专利

1. N-heterocyclic carbene-catalyzed fluorinated silyl-Reformatsky reaction of aldehydes with difluoro (trimethylsilyl) acetate [J] . Wang Ying, Xing Fen, Gu Cheng-Zhi, Tetrahedron . 2017,第30期

机译：用二氟（三甲基甲硅烷基）丙酸盐醛的N-杂环卡蛋烯催化氟化甲硅烷基重构醛反应
2. Chemo- and Diasteroselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-alpha-amino Aldehydes [J] . Haghshenas Pouyan, Gravel Michel Organic letters . 2016,第18期

机译：使用N-Boc-α-氨基醛类进行化学和非对映选择性N杂环碳催化的交叉联苯反应
3. Chemo- and Diasteroselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-alpha-amino Aldehydes [J] . Haghshenas Pouyan, Gravel Michel Organic letters . 2016,第18期

机译：使用N-Boc-α-氨基醛类进行化学和非对映选择性N杂环碳催化的交叉联苯反应
4. N-Heterocyclic Carbene-Catalyzed Synthesis of α-Amino Ketonesfrom in Situ-Produced Imines Derived from Aminals [C] . Justin Lamb, Ryo Takashima, Yumiko Suzuki 日本化学会春季年会 . 2020

机译：衍生自芳基的原位产生的亚胺中的N-杂环促α-氨基酮的合成
5. N-heterocyclic carbene-catalyzed reactions. [D] . Chiang, Pei-Chen. 2011

机译：N-杂环卡宾催化的反应。
6. Organocatalysis Special Feature: Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from αβ-unsaturated aldehydes for enantioselective Diels–Alder reactions [O] . Juthanat Kaeobamrung, Marisa C. Kozlowski, Jeffrey W. Bode 2010

机译：有机催化特性：手性N-杂环卡宾催化从αβ-不饱和醛生成烯醇酯等效物用于对映选择性Diels-Alder反应
7. N-Heterocyclic carbene-catalyzed domino hydroacylation/Stetter reactions of salicyl alkynylphosphonates and aromatic aldehydes [O] . Zhen-Qiang Wang, Ying Wang, Deqing Shi 2013

机译：N-杂环卡宾催化的多米诺加氢酰化/水杨基炔基膦酸酯和芳香醛的斯特特反应
8. Reactions of Carbon Monoxide with Trimethylsilyl and Tris(trimethylsilyl)silyl Derivatives of Group 4 Metals. Synthesis, Characterization, and Reactivity of Silaacyl Complexes [R] . Campion, B. K., Falk, J., Tilley, T. D. 1987

机译：一氧化碳与第3族金属的三甲基甲硅烷基和三（三甲基甲硅烷基）甲硅烷基衍生物的反应。 silaacyl配合物的合成，表征和反应性

N-heterocyclic carbene-catalyzed fluorinated silyl-Reformatsky reaction of aldehydes with difluoro (trimethylsilyl) acetate

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