Nickel-catalyzed alkyl-zincation and carboxylation of diynes
Literature Information
Publication Date
2016-10-08
DOI
10.1039/C6QO00484A
Impact Factor
5.281
Authors
Tao Cao
View Original
Abstract
A nickel-catalyzed three-component carbo-carboxylation of aryl-substituted diynes with ZnR2 and CO2 is described. With an ortho-ester functionality in the aryl group as the directing group, the usually observed hydrocarboxylation is completely suppressed with an unexpected CC bond isomerization. Based on the X-ray diffraction analysis and mechanistic study, it is believed that the reaction started with the oxidative addition with an aryl-substituted C–C triple bond and transmetalation with dialkyl zinc, followed by syn-carbonickelation with an alkyl-substituted C–C triple bond. Subsequent reductive elimination afforded the corresponding sp2-carbon zinc intermediate. Finally, the dynamic isomerization of a zinc-linked CC bond and the subsequent exclusive reaction of an isomerized sp2-carbon zinc intermediate with CO2 afforded the final carboxylic acids with a high stereoselectivity.
Recommended Journals
Related Literature
Furansversus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition–cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds
Yuanjing Xiao
2009-05-11
Communication
DOI: 10.1039/B905267D
Sequence selective dual-emission detection of (i, i + 1) bis-phosphorylated peptide using diazastilbene-type Zn(ii)-Dpa chemosensor‡
Yoshiyuki Ishida, Masa-aki Inoue, Tomonori Inoue, Akio Ojida, Itaru Hamachi
2009-04-24
Communication
DOI: 10.1039/B905814A
Solid-phase combinatorial synthesis of ester-type banana-shaped molecules by sequential palladium-catalyzed carbonylation
Sungmin Kang, Junji Watanabe, Takashi Takahashi
2009-03-23
Communication
DOI: 10.1039/B901788G
Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant
Keith M. Gligorich, Matthew S. Sigman
2009-05-14
Feature Article
DOI: 10.1039/B902868D
Azide groups in high oxidation state Mn carboxylate chemistry: a new Mn11 complex and its conversion to a Mn25azide complex with Me3SiN3
Theocharis C. Stamatatos, Alina Vinslava, Khalil A. Abboud, George Christou
2009-04-22
Communication
DOI: 10.1039/B902016K
Pair distribution function analysis of pressure treated zeolite Na-A
Jennifer E. Readman, Paul M. Forster, Karena W. Chapman, Peter J. Chupas, John B. Parise, Joseph A. Hriljac
2009-05-19
Communication
DOI: 10.1039/B902874A
Chimeric polymers formed from a monomer capable of free radical, oxidative and electrochemical polymerisation
Dhana Lakshmi, Michael J. Whitcombe, Frank Davis, Iva Chianella, Elena V. Piletska, Antonio Guerreiro, Sreenath Subrahmanyam, Paula S. Brito, Steven A. Fowler, Sergey A. Piletsky
2009-03-25
Communication
DOI: 10.1039/B821409C
Construction of trimeric porphyrin-fullerene-porphyrin stacks within surface-derived pores of nano-scale dimensions
Sheshanath V. Bhosale, Sidhanath V. Bhosale, Steven J. Langford, Dragan Krsta
2009-05-01
Communication
DOI: 10.1039/B903699G
Sonopotential: a new concept in electrochemistry
Elena Marchante, Teresa Lana-Villarreal, Verónica Sáez, José González-García, Roberto Gómez
2009-06-03
Communication
DOI: 10.1039/B908094E
You might also like
Compound Q&A
How should waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane be handled?
Waste containing (6-Bromo-2-naphthyl)oxy](dimethyl)(2-methyl-2-propanyl)silane (...
100751-65-3[(6-Bromo-2-naphthyl...
Compound Q&A
How is 7-Fluoro-4-isoquinolinecarboxylic acid (CAS: 1841081-40-0) typically synthesized?
7-Fluoro-4-isoquinolinecarboxylic acid can be synthesized via a multi-step proce...
1841081-40-07-Fluoro-4-isoquinol...
Compound Q&A
What are the physical and chemical properties of 2,3,5,6-Tetrabromothieno[3,2-b]thiophene (CAS: 124638-53-5)?
2,3,5,6-Tetrabromothieno[3,2-b]thiophene is a crystalline compound with a high m...
124638-53-52,3,5,6-Tetrabromoth...
Compound Q&A
Is 1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indole-4-carboxamide (CAS: 1542705-92-9) safe?
1-[4-(Benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indol...
1542705-92-91-[4-(Benzylamino)-7...
Compound Q&A
What is the market or research trend for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo- (CAS: 113942-30-6)?
The market for imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3...
113942-30-6Imidazo[5,1-d]-1,2,3...
Compound Q&A
What is 3-(Triisopropylsilyl)propiolaldehyde (CAS: 163271-80-5)?
3-(Triisopropylsilyl)propiolaldehyde is a synthetic organic compound with the CA...
163271-80-53-(Triisopropylsilyl...
Compound Q&A
What regulatory guidelines apply to 6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1)?
6-Nitro-2H-1,4-benzoxazin-3(4H)-one (CAS: 81721-87-1) is subject to various regu...
81721-87-16-Nitro-2H-1,4-benzo...
Compound Q&A
How should waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piperazinyl)acetic acid (CAS: 885272-91-3) be handled?
Waste containing (3-Fluorophenyl)(4-{[(2-methyl-2-propanyl)oxy]carbonyl}-1-piper...
885272-91-3(3-Fluorophenyl)(4-{...
Compound Q&A
What are the physical and chemical properties of N,N'-4,4'-Biphenyldiyldiisonicotinamide (CAS: 55119-40-9)?
N,N'-4,4'-Biphenyldiyldiisonicotinamide is a white crystalline solid with a mole...
55119-40-9N,N'-4,4'-Biphenyldi...
Compound Q&A
What industries use 6-Bromo-8-fluoro-2-quinazolinol (CAS: 1036756-15-6)?
6-Bromo-8-fluoro-2-quinazolinol is primarily used in the pharmaceutical industry...
1036756-15-66-Bromo-8-fluoro-2-q...
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane structure](https://static.chemtradehub.com/structs/567/56718-70-8-f037.webp "2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane structure")
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.