- Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes
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An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.
- Fan, Pei,Lan, Yun,Zhang, Chang,Wang, Chuan
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supporting information
p. 2180 - 2186
(2020/03/03)
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- Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles
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Modified reaction conditions that facilitate Pd-catalyzed alkene carboamination reactions of electron-deficient nitrogen nucleophiles are reported. Pent-4-enylamine derivatives bearing N-tosyl or N-trifluoroacetyl groups are coupled with aryl triflates to
- Peterson, Luke J.,Wolfe, John P.
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p. 2339 - 2344
(2015/07/27)
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- Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization
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(Chemical Equation Presented) We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)-H functionalization, a ffording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C - H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C - H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp3)-H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.
- Du, Wei,Gu, Qiangshuai,Li, Zhongliang,Yang, Dan
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p. 1130 - 1135
(2015/02/05)
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- Intramolecular aminocyanation of alkenes by N-CN bond cleavage
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A metal-free, Lewis acid promoted intramolecular aminocyanation of alkenes was developed. B(C6F5)3 activates N-sulfonyl cyanamides, thus leading to a formal cleavage of the N-CN bonds in conjunction with vicinal addition o
- Pan, Zhongda,Pound, Sarah M.,Rondla, Naveen R.,Douglas, Christopher J.
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supporting information
p. 5170 - 5174
(2014/05/20)
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- Synthesis of substituted tetrahydroindoloisoquinoline derivatives via intramolecular Pd-catalyzed alkene carboamination reactions
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Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed.
- Alicea, Jeremiah,Wolfe, John P.
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p. 4212 - 4217
(2014/05/20)
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- Intramolecular aminocyanation of alkenes by cooperative palladium/boron catalysis
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A cooperative palladium/triorganoboron catalyst to accomplish the intramolecular aminocyanation of alkenes through the cleavage of N-CN bonds is reported. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) is found to be crucial as a ligand for palladium to effectively catalyze the transformation with high chemo- and regioselectivity. A range of substituted indolines and pyrrolidines with both tetra- or trisubstituted carbon and cyano functionalities are readily furnished by the newly developed cyanofunctionalization reaction. A preliminary example of enantioselective aminocyanation is also described.
- Miyazaki, Yosuke,Ohta, Naoki,Semba, Kazuhiko,Nakao, Yoshiaki
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p. 3732 - 3735
(2014/04/03)
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- Synthetic study on tetrapetalones: Stereoselective cyclization of N-acyliminium ion to construct substituted 1-benzazepines
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The synthesis of the tetracyclic core of complex antibiotic tetrapetalones has been achieved In three steps starting from the simple Intermediate γ-hydroxy amide, which can be accessed through a high-yielding six-step sequence. The successful synthesis relies on a novel strategy based on the N-acyliminium ion cyclizatlon.
- Cheng, Li,Xlnyu, L.I. And,Ran, Hong
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supporting information; experimental part
p. 4036 - 4039
(2009/12/09)
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- Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation
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We have developed an efficient Pd(II)-catalyzed enantioselective oxidative tandem cyclization strategy using molecular oxygen as a green oxidant for the double 5-exo-trig cyclizations of N-(2-allylaryl) amides to afford a variety of indolines in good yiel
- Yip, Kai-Tai,Yang, Min,Law, Ka-Lun,Zhu, Nian-Yong,Yang, Dan
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p. 3130 - 3131
(2007/10/03)
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