Pd-catalyzed reactions of cyclopropanols, cyclobutanols and cyclobutenols

Bras, Jean Le; Мuzart, Jacques

doi:10.1016/j.tet.2019.130879

Cited by 30 publications

(14 citation statements)

References 146 publications

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“…Cyclopropanols [72][73][74][75] and the CF 3 group [48][49][50][51][52] are of broad interest because of their important applications in synthetic and medicinal chemistry. Therefore, (trifluoromethyl)cyclopropanol is potentially valuable because it contains these two important functional groups.…”

Section: Synpacts Synlettmentioning

confidence: 99%

Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Zhou¹,

Shen²

2022

Synlett

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The synthesis of common cyclopropenes has been widely studied, but the synthesis of cyclopropenols is a significant challenge. Herein, we highlight our recent work on the synthesis of trifluoromethylated cyclopropenols through [2+1] cycloaddition reaction between alkynes and trifluoroacetylsilanes under visible-light-induced organocatalysis. The novel amphiphilic donor-acceptor carbenes derived from trifluoroacetylsilanes can react effectively with both activated and unactivated alkynes. Broad substrate scope and good functional group tolerance have been achieved. Besides, the synthetic potential of this reaction was highlighted by a gram-scale reaction and the one-pot diastereoselective synthesis of trifluoromethylated cyclopropanols.

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Section: Synpacts Synlettmentioning

confidence: 99%

Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Zhou¹,

Shen²

2022

Synlett

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“… 31 − 37 For instance, they can participate in further intramolecular steps, or be cross-coupled with aryl-, 38 − 42 alkenyl-, 43 , 44 and alkynylhalides, 45 or propargylcarbonates, 46 among others. 29 , 47 , 48 Therefore, cyclopropyl- or cyclobutyl alcohols can behave as alkylating reagents under the appropriate conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Parallel studies have demonstrated the ability of Pd to perform the opening of strained cycloalkanols through β-carbon elimination ( b , Scheme ). , This process leads to a σ-alkyl-Pd(II) intermediate, which can evolve in different manners, depending on the substitution pattern of the cycloalkanol. − For instance, they can participate in further intramolecular steps, or be cross-coupled with aryl-, − alkenyl-, , and alkynylhalides, or propargylcarbonates, among others. ,, Therefore, cyclopropyl- or cyclobutyl alcohols can behave as alkylating reagents under the appropriate conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols

et al. 2022

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We report a Pd-catalyzed route to heterocycles bearing a tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by the C–C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate has been isolated and characterized by X-ray diffraction studies. Interestingly, the nature of the tethering alkynyl chain influences the E / Z stereochemistry of the alkenyl fragment in the functionalized heterocycles.

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“…[20][21][22] Three-membered cyclopropane motifs, a class of useful synthetic entities, are well-known applicable building blocks for C-C bond activation. [23][24][25] Since 2010, cyclopropanes, such as vinylcyclopropanes (VCPs) 26,27 and cyclopropanols, 28,29 have emerged as versatile synthons for C-H/C-C activation reactions. Generally, two different strategies based on the pathways of C-C cleavage in the catalytic system could be expected for the activation of cyclopropanes.…”

Section: Introductionmentioning

confidence: 99%

Merging C–H and C–C Activation in Pd(II)-Catalyzed Enantioselective Synthesis of Axially Chiral Biaryls

Chen

Liao

et al. 2021

CCS Chem

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The merging of C-H and C-C bond cleavage into one single chemical process remains a daunting challenge, especially in an asymmetric manner. Herein, a Pd(II)-catalyzed enantioselective tandem C-H/C-C activation for the synthesis of axially chiral biaryls is described. Two types of simple cyclopropanes, such as vinylcyclopropanes and cyclopropanols, were used as efficient and readily available coupling partners. This catalytic system features good functional group compatibility, excellent enantiocontrol (up to >99% ee) and the first use of palladium catalyst in this process. The synthetic utility of this protocol was demonstrated by gram-scale synthesis and further synthetic transformations to access various axially chiral biaryls with high enantiopurity. Two distinct but closely related C-C cleavage pathways of cyclopropanes were achieved in the enantioselective C-H/ C-C activation process, which represents a novel platform to further utilize the ring-opening attribute of cyclopropanes in asymmetric catalysis. Preliminary mechanistic studies provide insights into the role of cyclopropanols, which may pave the way for the development of novel catalytic transformations.

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Pd-catalyzed reactions of cyclopropanols, cyclobutanols and cyclobutenols

Cited by 30 publications

References 146 publications

Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols

Merging C–H and C–C Activation in Pd(II)-Catalyzed Enantioselective Synthesis of Axially Chiral Biaryls

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