Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling

Derosa, Joseph; Tran, Van Tan; Boulous, Mark N.; Chen, Jason S.; Engle, Keary M.

doi:10.1021/jacs.7b06567

Cited by 239 publications

(93 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to its prolific nature in stabilizing C(sp 3 )‐metallacycles, the Daugulis auxiliary has been extensively utilized in the regioselective functionalization of unactivated C(sp 3 )‐H bonds. In a recent example, Engle and coworkers exploited the powerful C(sp 3 )‐metallacycle stabilizing nature of the Daugulis auxiliary in a Ni‐catalyzed dicarbofunctionalization of olefins in 8‐aminoquinolinamides with aryl iodides and excess dialkylzinc reagents (Scheme ) …”

Section: Intermolecular Dicarbofunctionalization Of Olefinsmentioning

confidence: 99%

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Dhungana

Basnet

et al. 2018

The Chemical Record

356

114

View full text Add to dashboard Cite

Transition metal (TM)-catalyzed difunctionalization of unactivated olefins with two carbon-based entities is a powerful method to construct complex molecular architectures rapidly from simple and readily available feedstock chemicals. While dicarbofunctionalization of unactivated olefins has a long history typically with the use of either carbon monoxide to intercept C(sp )-[M] (alkyl-TM) species or substrates lacking in β-hydrogen (β-Hs), development of this class of reaction still remains seriously limited due to complications of β-H elimination arising from the in situ-generated C(sp )-[M] intermediates. Over the years, different approaches have been harnessed to suppress β-H elimination, which have led to the development of various types of olefin dicarbofunctionalization reactions even in substrates that generate C(sp )-[M] intermediates bearing β-Hs with a wide range of electrophiles and nucleophiles. In this review, these developments will be discussed both through the lens of historical perspectives as well as the strategies scrutinized over the years to address the issue of β-H elimination. However, this review article by no means is designed to be exhaustive in the field, and is merely presented to provide the readers an overview of the key reaction developments.

show abstract

Section: Intermolecular Dicarbofunctionalization Of Olefinsmentioning

confidence: 99%

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Dhungana

Basnet

et al. 2018

The Chemical Record

356

114

View full text Add to dashboard Cite

show abstract

“…Nickel is an inexpensive and sustainable transition metal, which was widely used in many transition metal‐catalyzed reactions due to the intrinsic properties of nickel catalyst . In 2017, The first example of Ni(0)‐catalyzed AQ‐directed intermolecular 1,2‐dicarbofunctionalization of unactivated alkenes successfully was developed by Engle group (Scheme ) . A variety of organozinc and aryl reagents were reactive as coupling partners in the standard conditions, affording an efficient synthetic method for β,γ ‐dicarbofunctionalization compounds.…”

Section: Difunctionalization Of Unactivated Alkenesmentioning

confidence: 99%

Recent Progress in Transition Metal‐Catalyzed Regioselective Functionalization of Unactivated Alkenes/Alkynes Assisted by Bidentate Directing Groups

Lin

Shen

2019

ChemCatChem

View full text Add to dashboard Cite

The catalytic functionalization of alkenes is among the most important and powerful methods for construction of two new bonds through cleavage of the π bonds, which is widely used for construction of numerous complex organic molecules. Recently, the strategy that involves directing groups-assisted regioselective functionalization of alkenes has found great synthetic application value, and great achievements have been made in the functionalization of unactivated alkenes and alkynes. This Minireview summarizes the recent progress in transition metal-catalyzed functionalization of unactivated alkenes and alkynes assisted by bidentate directing groups with high chemo-, regio-, and stereo-selectivity.[a] Dr. Scheme 1. Sequential carbopalladation of cyclooctadiene with a stoichiometric amount of PdCl 2 . Reproduced with permission from Ref. 8 a. . Regioselective carbopalladation of allylic amines with stoichiometric amount of Li 2 PdCl 4 . Reproduced with permission from Ref. 8 b. . Proposed mechanism of Ni(0)-catalyzed AQ-directed intermolecular 1,2-dicarbofunctionalization. Reproduced with permission from Ref. 22. Scheme 15. Ni-catalyzed three-component 1,2-dialkylation of unactivated alkenes. Reproduced with permission from Ref. 23. Scheme 16. Proposed mechanism of Ni-catalyzed three-component 1,2dialkylation of unactivated alkenes. Reproduced with permission from Ref. 23. Scheme 17. Pd(II)-catalyzed regioselective syn-hydroarylation of unactivated alkynes. Reproduced with permission from Ref. 26.

show abstract

“…In 2017, Engle et al demonstrated an ickel-catalyzed b,g-dicarbofunctionalization of alkenyl carbonyl compounds with aryl iodides and alkylzincs. [45] This reaction used ar emovable 8-aminoquinoline as ad irecting group, which led to the generation Scheme21. The palladium-catalyzed fluoroesterificationofs imple terminal alkenes.…”

Section: Nickel Catalysismentioning

confidence: 99%

Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

Zhang

Liu

Chen

et al. 2018

Chemistry An Asian Journal

221

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

Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling

Cited by 239 publications

References 48 publications

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Recent Progress in Transition Metal‐Catalyzed Regioselective Functionalization of Unactivated Alkenes/Alkynes Assisted by Bidentate Directing Groups

Transition‐Metal‐Catalyzed Three‐Component Difunctionalizations of Alkenes

Contact Info

Product

Resources

About