- Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides
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An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,
- Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling
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supporting information
p. 15903 - 15907
(2021/10/07)
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- Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond
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A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.
- Gevorgyan, Vladimir,Kurandina, Daria,Shing Cheung, Kelvin Pak,Yata, Tetsuji
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supporting information
p. 9932 - 9937
(2020/06/27)
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- Cu-Catalyzed highly regioselective 1,2-hydrocarboxylation of 1,3-dienes with CO2
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A practical copper-catalyzed highly regioselective 1,2-hydrocarboxylation of terminal 1,3-diene with carbon dioxide has been developed. Under mild reaction conditions, this chemistry afforded 2-benzyl-β,γ-unsaturated acid derivatives as products, which are a kind of important unit for bio-active molecules and versatile precursors for organic synthesis, with good functional group tolerance. The key intermediate in this transformation is illustrated by control experiments.
- Zhang, Penglin,Zhou, Zhanglang,Zhang, Rumeng,Zhao, Qian,Zhang, Chun
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supporting information
p. 11469 - 11472
(2020/10/12)
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- Nickel-catalyzed allyl-allyl coupling reactions between 1,3-dienes and allylboronates
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A regiospecific allyl-allyl coupling reaction between 1,3-dienes and allylboronates has been demonstrated under nickel catalysis. Salient features of this method include the earth-abundant metal catalyst, excellent regioselectivity and good functional group tolerance. Notably, even congested allyl substrates can also be applied to this protocol, thus allowing for the rapid preparation of a series of valuable 1,5-dienes. This journal is
- Ji, Ding-Wei,He, Gu-Cheng,Zhang, Wei-Song,Zhao, Chao-Yang,Hu, Yan-Cheng,Chen, Qing-An
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supporting information
p. 7431 - 7434
(2020/07/15)
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- Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
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Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
- Marcum, Justin S.,Roberts, Courtney C.,Manan, Rajith S.,Cervarich, Tia N.,Meek, Simon J.
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supporting information
p. 15580 - 15583
(2017/11/14)
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- Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
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We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.
- Adamson, Nathan J.,Hull, Ethan,Malcolmson, Steven J.
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supporting information
p. 7180 - 7183
(2017/06/05)
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- Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation
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A novel highly enantioselective aminomethylamination of conjugated dienes with aminals catalyzed by a chiral palladium complex ligated with BINOL-derived chiral diphosphinite has been successfully developed. This reaction proceeds via a Pd-catalyzed cascade C-N bond activation, aminomethylation, and asymmetric allylic amination reaction under mild reaction conditions, providing a unique and efficient strategy for the synthesis of enantiomerically pure allylic 1,3-diamines.
- Liu, Yang,Xie, Yinjun,Wang, Hongli,Huang, Hanmin
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supporting information
p. 4314 - 4317
(2016/05/09)
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- A highly selective synthesis of 1-substituted (E)-buta-1,3-dienes with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane as building block
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Highly selective synthesis of 1-substituted (E)-buta-1,3-dienes via palladium-catalyzed Suzuki-Miyaura cross-coupling of (E)-alkenyl iodides with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1) is reported. The vinylboronate pinacol ester (1) acts as a vinyl building block to show high chemoselectivity for the Suzuki-Miyaura pathway versus Heck coupling in the presence of biphasic conditions (Pd(PPh3)4, aqueous K 2CO3, toluene and ethanol). Copyright
- Szudkowska-Fratczak, Justyna,Ryba, Aline,Franczyk, Adrian,Walkowiak, Jedrzej,Kubicki, Maciej,Pawluc, Piotr
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p. 137 - 139
(2014/03/21)
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- Titanium-catalyzed intermolecular hydroaminoalkylation of conjugated dienes
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Ti me kangaroo down: Conjugated dienes undergo intermolecular hydroaminoalkylation in the presence of Ti catalyst [Ind2TiMe 2] (Ind=η5-indenyl). This new reaction offers a highly atom-efficient approach to homoallylic amines from 1,3-butadienes. Copyright
- Preuss, Till,Saak, Wolfgang,Doye, Sven
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p. 3833 - 3837
(2013/04/24)
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- Stereoselective synthesis of dienes from N-allylhydrazones
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(Chemical Equation Presented) A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed. High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienoph
- Mundal, Devon A.,Lutz, Kelly E.,Thomson, Regan J.
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supporting information; experimental part
p. 465 - 468
(2009/07/11)
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