Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds

Kimura, Masanari; Matsuo, Shintaro; Shibata, Kazufumi; Tamaru, Yoshinao

doi:10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w

Cited by 92 publications

(34 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1999, Tamaru and coworkers reported a nickel(0)‐catalyzed three‐component connection reaction of 1,3‐dienes with dimethylzinc reagent and aldehydes to provide homoallyl alcohols (Scheme 4). [ 49 ] The proposed mechanism involved an oxidative cyclization between nickel(0)‐diene complex and aldehyde as well as the sequential cross‐coupling with dimethylzinc reagent. Later on, the substrate scope of the electrophiles was extended to various ketones and imines to yield homoallylamines.…”

Section: Intermolecular Dicarbofunctionalization Of Alkenesmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

View full text Add to dashboard Cite

As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctionalization of alkenes through a historical perspective, including intermolecular three-component reactions and intramolecular cascade reactions. Among the pathways discussed in this review, the carbometallation/cross-coupling process and the radical addition/cross-coupling process are the two major pathways for the nickel-catalyzed dicarbofunctionalization of alkenes. The oxidative cyclization and 1,2-metallate shift processes are also selectively discussed. These methods overcome the limitations associated with the reactions using noble metals in the field, providing an efficient and straightforward access to structurally diversified molecules. Yun-Cheng Luo (right) received his BSc degree in 2016 and master degree in 2019 from University of Science and Technology of China. Then he joined Professor Xingang Zhang's group at Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences to pursue his doctorate in organic chemistry. His research interests are focused on the activation of inert C-H or C-X bonds of bulky chemicals and their applications in the synthesis of fluorine-containing compounds. Chang Xu (middle) obtained his BSc degree in basic pharmacy from China Pharmaceutical University (China) in 2015. With an interest in organic chemistry and medicinal chemistry, he then began his graduate studies at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences under the supervision of Professor Xingang Zhang. His research interests are focused on the activation and transformations of fluoroalkylanes and their applications in medicinal chemistry. Xingang Zhang (left) obtained his BSc degree in 1998 from Sichuan University (China) and received the Ph.D. in 2003 at Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008, and became research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology.

show abstract

Section: Intermolecular Dicarbofunctionalization Of Alkenesmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

View full text Add to dashboard Cite

show abstract

“…found that nickel complexes could be used as catalysts in the transformation of 1,3‐butadienes. For example, 1,4‐dicarbofunctionalization with dimethylzinc and aldehydes mediated by [Ni(acac) 2 ] to give the corresponding allyl alcohols was reported in 1999 (Scheme ) . When aromatic aldehydes were used as an electrophile, the 1,4‐difunctionalized products were generated selectively, whereas dimerization and 1,8‐difunctionalized products could be produced to some extent with aliphatic aldehydes.…”

Section: Nickel Catalysismentioning

confidence: 99%

Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

Zhang

Liu

Chen

et al. 2018

Chemistry An Asian Journal

244

View full text Add to dashboard Cite

Three-component reactions can directly convert three reactants into the desired products in one pot and thus greatly shorten the synthetic path. Recently, transition-metal catalysis has been applied in the difunctionalization of alkenes and remarkable progress has been achieved to facilitate the construction of a wide range of functional molecules with high atom- and step-economic efficiency. This Focus Review highlights recent advances in this field.

show abstract

“…The methyl group of Me 2 Zn and an aldehyde add to a diene in 1,4-fashion and provide a homoallyl alcohol 5.27 in good yield (Eq. (5.12)) [44]. For example, benzaldehyde, 1,3-butadiene, and Me 2 Zn combine one with another linearly in this sequence in a 1:1:1 ratio to provide (E)-3-phenyl-3-hexen-1-ol 5.27 in quantitative yield.…”

Section: Allylation Of Aldehydes Promoted By Dimethylzinc Trimethybomentioning

confidence: 99%

Reaction of Dienes and Allenes

Kimura

Tamaru

2005

Modern Organonickel Chemistry

Self Cite

View full text Add to dashboard Cite

1,3-Butadiene and isoprene (2-methyl-1,3-butadiene) are among the most important building blocks both in the laboratory and in the chemical industry. 1,3-Butadiene (DH f ¼ þ26:1) and 1,2-butadiene (methylallene DH f ¼ þ38:8) are highly unsaturated and labile even toward relatively unreactive reagents, such as O 2 in air, and undergo polymerization during storage.Although the [4þ2]cycloaddition -the so-called Diels-Alder reaction -of butadiene to afford 4-vinylcyclohexene is a thermally permitted process, it only proceeds under harsh conditions (e.g., at 250 C under high pressure). In contrast, nickel complexes promote the [4þ2]cycloaddition under milder conditions (e.g., at 0 C under ambient pressure) [1]. Furthermore, the complexes even promote thermally forbidden [4þ4]cycloaddition and other reactions. Many other 1,3-dienes and allenes are also subject to dimerization, oligomerization, and polymerization under nickel catalysis, and hence serve as useful C4 and C3 carbon resources for a variety of organic syntheses.This chapter deals with recent developments in the nickel-catalyzed functionalizations of conjugated dienes and allenes, and incorporates the following topics: 1) dimerization and polymerization; 2) allylic and homoallylic alkylation of carbonyl compounds (dienes and allenes as nucleophiles); and 3) 1,2-and 1,4-addition reactions of reagents X-Y toward dienes and allenes. 5.1Dimerization and Polymerization of 1,3-Dienes Nickel complexes are extremely effective catalysts for the dimerization and polymerization of dienes. The catalytic reactions are described in Chapter 6, Section 6.4. The major subject of this section relates to the structures and reactivities of Ni(II)Á(butadiene) 2 complexes (the stoichiometric reactions) and recent developments in the field of polymerization.Modern Organonickel Chemistry. Edited by Y. Tamaru

show abstract

Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds

Cited by 92 publications

References 4 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

Reaction of Dienes and Allenes

Contact Info

Product

Resources

About

Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds

Cited by 92 publications

References 4 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

Reaction of Dienes and Allenes

Contact Info

Product

Resources

About

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†