Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Yang, Bo; Wang, Zhong‐Xia

doi:10.1021/acs.joc.6b02564

Cited by 42 publications

(22 citation statements)

References 65 publications

(39 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Although the detailed reaction mechanism for the nickel catalyzed allyl-aryl coupling reaction was not clear, a plausible mechanism is proposed in Scheme 3 [13,28]. Initially, nickel(II) complex 1b is converted into anionic nickel(0) species I through its reaction with at least 2 equivalents of arylmagnesium reagent accompanied by the formation of a biaryl.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex

et al. 2019

View full text Add to dashboard Cite

A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.

show abstract

Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C{ 1 H} NMR spectra have been attached in the Supplementary Materials. The product was characterized by comparison with the previously reported 1 H and 13 C{ 1 H} NMR data [28].…”

Section: Methodsmentioning

confidence: 99%

Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex

et al. 2019

View full text Add to dashboard Cite

show abstract

“…[Cp*RhCl 2 ] 2 was purchased from Aladdin Industrial Corporation. Allylic alcohols were prepared according to reported procedures . Alkenylpyridines, [Cp*Rh(SbF 6 ) 2 ](MeCN) 3 , [Cp*Rh(OTf) 2 ](MeCN) 3 , 2‐cyclohexenylpyrimidine, 1‐cyclohexenyl‐1 H ‐pyrazole, cyclohexenyl(pyrrolidin‐1‐yl)methanone, and N ‐methoxycyclohex‐1‐enecarboxamide were prepared according to reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Rhodium‐Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Yan

Wang

2017

Asian J Org Chem

Self Cite

View full text Add to dashboard Cite

Cp*RhCl 2 ] 2 was demonstrated to catalyzet he oxidative coupling of alkenylpyridines with allylic alcohols through alkenyl CÀHa ctivation in the presence of AgOTf and AgOAc to afford b-alkenyl ketones and aldehydes in moderate to good yields. Allylica lcohol, 1-aryl and 1-alkyl allylic alcohols can be coupled with various alkenylpyridines. The reactiono ccurred at the g-position of allylic alcohols and the cis-b-position of the alkenylpyridines.Scheme1.Sp 2 CÀHa ctivationand couplingwith allylic alcohols.[a] R. 1 HNMR (400 MHz, CDCl 3 ): d = 9.60 (s, 1H), 8.56 (d, J = 4.7 Hz, 1H), 7.60 (t, J = 7.9 Hz, 1H), 7.16-7.02 (m, 2H), 2.58-2.41 (m, 4H), 2.36-2.18 (m, 4H), 1.72-1.43 ppm (m, 8H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): d = HR-MS (ESI): m/z = 244.1698 [M+ +H] + ,c alcd for C 16 H 21 NO 244.1696. 4-(2-(Pyridin-2-yl)cyclooct-1-en-1-yl)butan-2-one (3 cc):E lution with EtOAc/petroleum ether 1:2( v/v), colorless oil, yield:7 3.0 mg (71 %). 1 HNMR (400 MHz, CDCl 3 ): d = 8.56-8.52 (m, 1H), 7.57 (dt, J = 7.7, 1.8 Hz, 1H), 7.13-7.02 (m, 2H), 2.53-2.40 (m, 4H), 2.32-2.22 (m, 2H), 2.20-2.10 (m, 2H), 1.97 (s, 3H), 1.66-1.42 ppm (m, 8H);

show abstract

“…In this context, low cost and highly abundant nickel appears to be the ideal catalyst for these transformations . Nickel‐catalyzed Negishi cross‐couplings, Suzuki cross‐couplings, allylic aminations, and alkylations with unprotected allylic alcohols have been demonstrated. A nickel‐catalyzed cyanation reaction was reported by Rousseaux and co‐workers using allylic pivalate esters as electrophiles to access allylic nitriles (Scheme a) .…”

Section: Figurementioning

confidence: 99%

Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Long

Gao

et al. 2020

Angew Chem Int Ed

View full text Add to dashboard Cite

Enantioselective auto‐tandem catalysis represents a challenging yet highlight attractive topic in the field of asymmetric catalysis. In this context, we describe a dual catalytic cycle that merges allylic cyanation and asymmetric hydrocyanation. The one‐pot conversion of a broad array of allylic alcohols into their corresponding 1,3‐dinitriles proceeds in good yield with high enantioselectivity. The products are densely functionalized and can be easily transformed to chiral diamines, dinitriles, diesters, and piperidines. Mechanistic studies clearly support a novel sequential cyanation/hydrocyanation pathway.

show abstract

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Cited by 42 publications

References 65 publications

Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex

Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex

Rhodium‐Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Contact Info

Product

Resources

About