Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

被引:26
作者
Ajvazi, Njomza [1 ]
Stavber, Stojan [1 ,2 ]
机构
[1] Jozef Stefan Int Postgrad Sch, Jamova 39, Ljubljana 1000, Slovenia
[2] Jozef Stefan Inst, Jamova 39, Ljubljana 1000, Slovenia
关键词
Alcohols; C-C or C-heteroatom bond formation; nucleophilic substitution; BETA-DICARBONYL COMPOUNDS; ONE-POT SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION-REACTIONS; PI-ACTIVATED ALCOHOLS; CATALYZED DIRECT BENZYLATION; DIRECT COUPLING REACTION; MILD REACTION CONDITIONS; SECONDARY BENZYLIC ALCOHOLS; DIPHENYLMETHYL DPM ETHERS; FRIEDEL-CRAFTS ALKYLATION;
D O I
10.24820/ark.5550190.p010.237
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In recent years, nucleophilic substitution of alcohols leading to the formation of the C-C and C-heteroatom bonds has become an attractive process used in the synthesis of organic compounds, offering a potential impact on the environment, since water is the only by-product of the reaction. A comprehensive compilation of methods for the activation and displacement of a hydroxyl group covering the last seventeen years is the objective of the present review.
引用
收藏
页码:288 / 329
页数:42
相关论文
共 214 条
[31]   Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide [J].
Chen, Shu-jie ;
Lu, Guo-ping ;
Cai, Chun .
SYNTHESIS-STUTTGART, 2015, 47 (07) :976-984
[32]   One-Pot Palladium-Catalyzed Borrowing Hydrogen Synthesis of Thioethers [J].
Corma, Avelino ;
Navas, Javier ;
Rodenas, Tania ;
Sabater, Maria J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (51) :17464-17471
[33]   A rational approach towards the nucleophilic substitutions of alcohols "on Water" [J].
Cozzi, Pier Giorgio ;
Zoli, Luca .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4162-4166
[34]   Water compatible gold(III)-catalysed synthesis of unsymmetrical ethers from alcohols [J].
Cuenca, Ana B. ;
Mancha, Gisela ;
Asensio, Gregorio ;
Medio-Simon, Mercedes .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (05) :1518-1523
[35]   Development of a General Non-Noble Metal Catalyst for the Benign Amination of Alcohols with Amines and Ammonia [J].
Cui, Xinjiang ;
Dai, Xingchao ;
Deng, Youquan ;
Shi, Feng .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (11) :3665-3675
[36]   Microwave assisted benzylation of naphthols and 4-hydroxycoumarin under catalyst & solvent free conditions [J].
Dada, Ravikrishna ;
Singh, Garima ;
Pareek, Abhishek ;
Kausar, Saeen ;
Yaragorla, Srinivasarao .
TETRAHEDRON LETTERS, 2016, 57 (33) :3739-3742
[37]   First example of a heterobimetallic 'Pd-Sn' catalyst for direct activation of alcohol: efficient allylation, benzylation and propargylation of arenes, heteroarenes, active methylenes and allyl-Si nucleophiles [J].
Das, Debjit ;
Pratihar, Sanjay ;
Roy, Ujjal Kanti ;
Mal, Dipakranjan ;
Roy, Sujit .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (23) :4537-4542
[38]   Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction [J].
Denton, Ross M. ;
An, Jie ;
Adeniran, Beatrice ;
Blake, Alexander J. ;
Lewis, William ;
Poulton, Andrew M. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6749-6767
[39]   Taming furfuryl cations for the synthesis of privileged structures and novel scaffolds [J].
Dhiman, Seema ;
Ramasastry, S. S. V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (26) :4299-4303
[40]   Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates [J].
Ding, Rui ;
He, Yong ;
Wang, Xiao ;
Xu, Jingli ;
Chen, Yurong ;
Feng, Man ;
Qi, Chuanmin .
MOLECULES, 2011, 16 (07) :5665-5673