Concerted Nucleophilic Aromatic Substitution Reactions

被引：213

作者：

Rohrbach, Simon ^{[1
]}

Smith, Andrew J. ^{[1
]}

Pang, Jia Hao ^{[2
]}

Poole, Darren L. ^{[3
]}

Tuttle, Tell ^{[1
]}

Chiba, Shunsuke ^{[2
]}

Murphy, John A. ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[3] GlaxoSmithKline Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 46期

基金：

英国工程与自然科学研究理事会;

关键词：

concerted reactions; cS(N)Ar mechanism; Meisenheimer complex; nucleophilic aromatic substitution; NEWMAN-KWART REARRANGEMENT; ONE-POT SYNTHESIS; SMILES REARRANGEMENT; AB-INITIO; TRIGONAL CARBON; SNAR REACTION; GAS-PHASE; MECHANISM; DISPLACEMENT; IONS;

D O I：

10.1002/anie.201902216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recent developments in experimental and computational chemistry have identified a rapidly growing class of nucleophilic aromatic substitutions that proceed by concerted (cS(N)Ar) rather than classical, two-step, SNAr mechanisms. Whereas traditional SNAr reactions require substantial activation of the aromatic ring by electron-withdrawing substituents, such activating groups are not mandatory in the concerted pathways.

引用

页码：16368 / 16388

页数：21

共 137 条

[1] Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids [J].

Abas, Hossay ;

Mas-Rosello, Josep ;

Amer, Mostafa Mahmoud ;

Durand, Derek J. ;

Groleau, Robin R. ;

Fey, Natalie ;

Clayden, Jonathan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) :2418-2422

[2] Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles [J].

Adouama, Cherif ;

Buden, Maria E. ;

Guerra, Walter D. ;

Puiatti, Marcelo ;

Joseph, Benoit ;

Barolo, Silvia M. ;

Rossi, Roberto A. ;

Medebielle, Maurice .

ORGANIC LETTERS, 2019, 21 (01) :320-324

[3] INTERACTION OF PENTAFLUOROPYRIDINE WITH 4-NITROPHENOL AND PENTAFLUOROPHENOL IN THE PRESENCE OF POTASSIUM FLUORIDE AND 18-CROWN-6-ETHER [J].

AKSENOV, VV ;

VLASOV, VM ;

YAKOBSON, GG .

JOURNAL OF FLUORINE CHEMISTRY, 1982, 20 (04) :439-458

[4] Synthesis of an octahydro-1,1′-binaphthyl thioether ligand and comparison with unhydrogenated binaphthyl analogues [J].

Albrow, V ;

Biswas, K ;

Crane, A ;

Chaplin, N ;

Easun, T ;

Gladiali, S ;

Lygo, B ;

Woodward, S .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2813-2819

[5] A STUDY OF THE SCHONBERG REARRANGEMENT OF DIARYL THIONCARBONATES TO DIARYL THIOLCARBONATES [J].

ALKAZIMI, HR ;

TARBELL, DS ;

PLANT, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (09) :2479-2482

[6]

[Anonymous], 2017, ANGEW CHE

[7]

[Anonymous], ANGEW CHEM

[8] SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES [J].

ARTAMKINA, GA ;

EGOROV, MP ;

BELETSKAYA, IP .

CHEMICAL REVIEWS, 1982, 82 (04) :427-459

[9] Intramolecular arylation of amino acid enolates [J].

Atkinson, Rachel C. ;

Leonard, Daniel J. ;

Maury, Julien ;

Castagnolo, Daniele ;

Volz, Nicole ;

Clayden, Jonathan .

CHEMICAL COMMUNICATIONS, 2013, 49 (84) :9734-9736

[10]

Austen P.T., 1876, Berichte Dtsch. Chem. Ges, V9, P621, DOI DOI 10.1002/CBER.187600901190

← 1 2 3 4 5 6 7 8 9 10 →