Iron-catalyzed oxidative bis-arylation of indolin-2-ones for direct construction of quaternary carbons

The cross-dehydrogenative coupling protocol is catalyzed by a simple iron salt, and air is used as the terminal oxidant under very mild conditions, offering a novel synthetic method for the direct construction of all-carbon quaternary centers.

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Direct Synthesis of Vicinal Tricarbonyl Amides by Coupling of α-Oxo Acid Chlorides with Carbamoylsilanes

Synthesis ◽

10.1055/s-0037-1611778 ◽

2019 ◽

Vol 51 (15) ◽

pp. 2977-2983

Author(s):

Yuling Han ◽

Yuping Li ◽

Shenghua Han ◽

Pengpeng Zhang ◽

Jianxin Chen

Keyword(s):

Oxalyl Chloride ◽

Direct Synthesis ◽

Coupling Reaction ◽

Cross Coupling ◽

Synthetic Method ◽

Acid Chlorides ◽

Mild Conditions ◽

Cross Coupling Reaction ◽

The Cross

A convenient synthetic method for vicinal tricarbonyl amides by the cross-coupling reaction of α-oxo acid chlorides with carbamoylsilanes is developed. The reaction tolerates a broad range of substituents on the amido nitrogen of carbamoylsilanes, and directly affords good yields of vicinal tricarbonyl amides under mild conditions without use of oxidants. The reaction of carbamoylsilanes with oxalyl chloride has also been explored, and is accompanied by decarbonylation to give vicinal tricarbonyl amides.

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Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates

10.26434/chemrxiv.12102678 ◽

2020 ◽

Author(s):

Albert Granados ◽

Anna Balleteros ◽

Adelina Vallribera

Keyword(s):

Hypervalent Iodine ◽

Catalytic Method ◽

Quaternary Centers ◽

Mild Conditions ◽

Reaction Proceeds ◽

Mechanistic Investigations ◽

Derivatives Of

An electrophilic enantioselective catalytic method for the a-pentafluoroethylation of alkyl 1-indanone-2-carboxylates is described. Under the use of La(OTf)3 in combination with (S,R)-indanyl-pybox ligand good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions leading to the formation of enantioenriched quaternary centers. This methodology uses an hypervalent iodine(III)-CF2CF3 reagent and mechanistic investigations are consistent with the involvement of a radical pathway.

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Synthesis of β-hydroxy-α-amino acid derivatives by the cross-dehydrogenative coupling of N-arylglycine esters with α-hydroxy ketones

Tetrahedron ◽

10.1016/j.tet.2021.132491 ◽

2021 ◽

pp. 132491

Author(s):

JunJiao Wang ◽

Yuyu Lv ◽

Yongwei Shang ◽

Zhoubin Deng ◽

Jianzhong Zhang ◽

...

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Dehydrogenative Coupling ◽

Hydroxy Ketones ◽

The Cross

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ChemInform Abstract: The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations

ChemInform ◽

10.1002/chin.201417278 ◽

2014 ◽

Vol 45 (17) ◽

pp. no-no

Author(s):

Simon A. Girard ◽

Thomas Knauber ◽

Chao-Jun Li

Keyword(s):

Dehydrogenative Coupling ◽

The Cross

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One-Pot Synthesis of α-Substituted Acrylates

SynOpen ◽

10.1055/s-0037-1610357 ◽

2018 ◽

Vol 02 (02) ◽

pp. 0161-0167

Author(s):

Magdalini Matziari ◽

Yixin Xie

Keyword(s):

Amino Acids ◽

Reaction Times ◽

Synthetic Method ◽

One Pot ◽

Biologically Relevant ◽

Mild Conditions ◽

One Pot Synthesis ◽

Acrylic Esters ◽

Natural Amino Acids ◽

Work Up

A simple and efficient synthetic method towards α-substituted acrylic esters has been developed using the Horner–Wadsworth–Emmons (HWE) reaction with HCHO after alkylation of phosphonoacetates in a one-pot reaction. This method allows the smooth introduction of various side-chains, such as natural amino acids and other biologically relevant substituents. The use of mild conditions, inexpensive reagents, short reaction times and simple work-up and purification steps provides an effective and general alternative to cumbersome multistep and low-yielding procedures described to date.

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Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with diverse carbon pronucleophiles: facile access to functionalized tetrahydroquinolines

Chemical Communications ◽

10.1039/d0cc02921a ◽

2020 ◽

Vol 56 (53) ◽

pp. 7333-7336

Author(s):

Guangzhe Li ◽

Chengdong Wang ◽

Yueqing Li ◽

Kun Shao ◽

Guo Yu ◽

...

Keyword(s):

Synthetic Method ◽

Dehydrogenative Coupling

Redox cross-dehydrogenative coupling of N-propargylanilines with diverse carbon pronucleophiles offers a general and efficient synthetic method to construct functionalized tetrahydroquinolines.

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Direct Dehydrogenative Coupling of Alcohols with Hydrosilanes Promoted by Sodium tri(sec-butyl)borohydride

Catalysts ◽

10.3390/catal8120618 ◽

2018 ◽

Vol 8 (12) ◽

pp. 618 ◽

Cited By ~ 2

Author(s):

Maciej Skrodzki ◽

Maciej Zaranek ◽

Samanta Witomska ◽

Piotr Pawluc

Keyword(s):

Organic Synthesis ◽

Catalytic System ◽

Mild Conditions ◽

Dehydrogenative Coupling ◽

Stoichiometric Reaction ◽

Work Up

Alkoxysilanes find application in many areas of chemistry ranging from research-scale organic synthesis to multi-ton production of materials. Classically, they are obtained in stoichiometric reaction of alcoholysis of chlorosilanes, however, recent years brought development in the field of direct dehydrogenative coupling of hydrosilanes with alcohols, which is a more atom-economic and benign alternative to the former process. In this paper, we report the use of sodium tri(sec-butyl)borohydride as a convenient promoter of this reaction. Exemplary syntheses carried out under mild conditions and without additional solvents, followed by very easy work-up procedure, show excellent potential for application of so devised catalytic system.

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Construction of trifluoromethylated quaternary stereocenters via p-quinone methides

Chemical Communications ◽

10.1039/c9cc08936e ◽

2020 ◽

Vol 56 (20) ◽

pp. 3031-3034 ◽

Cited By ~ 3

Author(s):

Kyu Terashima ◽

Tomoko Kawasaki-Takasuka ◽

Tomohiro Agou ◽

Toshio Kubota ◽

Takashi Yamazaki

Keyword(s):

Synthetic Method ◽

Quinone Methides ◽

Quaternary Centers ◽

Quaternary Stereocenters

Development of a new synthetic method for the construction of quaternary centers with a CF3 group was realized by way of 1,6-addition of various nucleophiles to highly reactive δ-trifluoromethylated p-quinone methides generated in situ.

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