Nickel-catalyzed dynamic kinetic cross-electrophile coupling of benzylic alcohols and alkenyl triflates

Literature Information

Publication Date 2023-11-14
DOI 10.1039/D3QO01416A
Impact Factor 5.281
Authors

Xuejing Peng, Jingxian Huang, Guan-Yu Han, Xing-Zhong Shu


View Original

Abstract

The direct deoxy-functionalization of alcohols through cross-coupling is synthetically appealing but remains a challenging task. In this manuscript, we report a dynamic kinetic cross-electrophile coupling reaction between benzylic alcohols and alkenyl triflates. This mild reaction enables the replacement of the alcohol group with an alkenyl functionality, yielding versatile benzyl-substituted cyclic alkenes. The production of cyclic alkenes makes the method orthogonal to the existing reductive coupling methodologies, which are mainly effective in producing acyclic derivatives. Functional groups such as ester, phenol, indole, heterocycle, and boronic ester are tolerated.

Related Literature

Contents list

Front/Back Matter

DOI: 10.1039/C4CP90005G

X-ray absorption spectroscopy and resonant inelastic scattering study of the first lithiation cycle of the Li-ion battery cathode Li2−xMnSiO4

M. Dahbi, T. Gustafsson, K. Edström, D. Newby, K. E. Smith, L.-C. Duda

2013-12-18 Paper

DOI: 10.1039/C3CP54103G

Large splittings of the 4f shell of Ce3+ in garnets

2013-11-25 Paper

DOI: 10.1039/C3CP53549E

Plasmon-enhanced water splitting on TiO2-passivated GaP photocatalysts

Jing Qiu, Guangtong Zeng, Prathamesh Pavaskar, Zhen Li

2013-12-20 Paper

DOI: 10.1039/C3CP54674H

Carbon-coated LiCrTiO4 electrode material promoting phase transition to reduce asymmetric polarization for lithium-ion batteries

Bo Yan, Jing Ye, Xue Li, Yansheng Liu, Haiping You

2013-11-19 Paper

DOI: 10.1039/C3CP54399D

Shape selectivity using ionic liquids for the preparation of silver and silver sulphide nanomaterials

Amol B. Patil, Bhalchandra M. Bhanage

2013-12-16 Paper

DOI: 10.1039/C3CP54382J

Spectromicroscopic evidence of interstitial and substitutional dopants in association with oxygen vacancies in Sm-doped ceria nanoparticles

Shih-Yun Chen, Ren-Jie Chen, William Lee, Chung-Li Dong, Alexandre Gloter

2014-01-06 Paper

DOI: 10.1039/C3CP54613F

Exploring and rationalising effective n-doping of large area CVD-graphene by NH3

G. V. Bianco, M. Losurdo, M. M. Giangregorio, P. Capezzuto, G. Bruno

2013-12-16 Paper

DOI: 10.1039/C3CP54451F

Slow deactivation channels in UV-photoexcited adenine DNA

Xuebo Chen, Weihai Fang, Haobin Wang

2014-01-02 Paper

DOI: 10.1039/C3CP55020F

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

Source Journal

Organic Chemistry Frontiers

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

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.