CF3-Containing para-Quinone Methides for Organic Synthesis

被引：15

作者：

Winter, Michael ^{[1
]}

Schuetz, Roman ^{[1
]}

Eitzinger, Andreas ^{[1
]}

Ofial, Armin R. ^{[2
]}

Waser, Mario ^{[1
]}

机构：

[1] Johannes Kepler Univ Linz, Inst Organ Chem, Altenbergerstr 69, A-4040 Linz, Austria

[2] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandrstr 5-13, D-81377 Munich, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 25期

关键词：

Quinone methides; Trifluoromethylation; Electrophilicity; Kinetics; Phase-transfer catalysis; ASYMMETRIC 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYTIC 1,6-ADDITION; NUCLEOPHILIC REACTIVITIES; SULFONIUM SALTS; ACID-ESTERS; TRIFLUOROMETHYLATION; ACCESS; SPIROCYCLOPROPANATION; COMBINATIONS;

D O I：

10.1002/ejoc.202000295

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new family of CF3-containing para-quinone methides (CF3-QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF3-containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF3-QM 2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one was determined to be -11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.

引用

页码：3812 / 3817

页数：6

共 50 条

[21] Organic Semiconductor Devices Fabricated with Recycled Tetra Pak®-Based Electrodes and para-Quinone Methides
Vergara, Maria Elena Sanchez
Esquivel, Eva Alejandra Santillan
Ballinas-Indili, Ricardo
Lozada-Flores, Octavio
Miranda-Ruvalcaba, Rene
Alvarez-Toledano, Cecilio
COATINGS, 2024, 14 (08)
[22] Phosphine-catalysed transformations of ortho- and para-quinone methides
Maestro, Aitor
Zurro, Mercedes
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (41) : 8244 - 8258
[23] Electrochemical Reductive Carboxylation of para-Quinone Methides with CO2
Yan, Yunying
Li, Haiqiong
Xie, Fenfen
Lu, Wenhua
Zhang, Zhengbing
Jing, Linhai
Han, Pan
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3830 - 3836
[24] Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with para-Quinone Methides
Song, Zefeng
Wang, Weijia
Liu, Zhixin
Lu, Yue
Wang, De
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13): : 8590 - 8599
[25] Synthesis of spiroindolenine-bearing chroman scaffolds based on a cyclization reaction of para-Quinone methides
Qin, Hongmei
Xie, Qimei
He, Long
NEW JOURNAL OF CHEMISTRY, 2022, 46 (21) : 9985 - 9988
[26] Design, synthesis and antitumor activity of potent and safe para-quinone methides derivatives in vitro and in vivo
Li, Pengxiao
Ma, Yazhong
Wang, Ke
Shi, Xiaohan
Yang, Jie
Liu, Guoyun
BIOMEDICINE & PHARMACOTHERAPY, 2022, 156
[27] Acid-Catalyzed Regioselective Synthesis of α-Diarylmethyl Substituted Phenols and para-Quinone Methides in Water
Xiong, Biquan
Shang, Wenli
Xu, Weifeng
Liu, Yu
Tang, Ke-Wen
Wong, Wai-Yeung
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)
[28] Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para-quinone methides
Wong, Yuk Fai
Wang, Zhaobin
Sun, Jianwei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5751 - 5754
[29] Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to para-Quinone Methides
Ali, Amjad
Jajoria, Raveena
Harit, Harish K.
Singh, Ravi P.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (08): : 5213 - 5228
[30] Synthesis of para-Quinone Methides via Oxidative Ring-Opening of Spiro-cyclopropanyl-cyclohexadienones
Cui, Chaoxing
Wu, Jianli
Song, Xixi
Li, Miaomiao
SYNTHESIS-STUTTGART, 2022, 54 (21): : 4802 - 4809

← 1 2 3 4 5 →