Unactivated C(sp3)–H hydroxylation through palladium catalysis with H2O as the oxygen source

2015 ◽  
Vol 51 (80) ◽  
pp. 14929-14932 ◽  
Author(s):  
Jiantao Hu ◽  
Tianlong Lan ◽  
Yihua Sun ◽  
Hui Chen ◽  
Jiannian Yao ◽  
...  
Keyword(s):  
Functional Group ◽  
Palladium Catalysis ◽  
Hydroxyl Group ◽  
Palladium Catalyzed ◽  
Conventional Methods

A novel palladium catalyzed hydroxylation of unactivated aliphatic C(sp3)–H bonds was successfully developed. Different from conventional methods, water serves as the hydroxyl group source in the reaction. This reaction demonstrates broad functional group tolerance.

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)–H bonds at room temperature

2016 ◽  
Vol 52 (38) ◽  
pp. 6423-6426 ◽  
Author(s):  
Xinglin Yang ◽  
Yonghui Sun ◽  
Tian-yu Sun ◽  
Yu Rao
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Palladium Catalysis ◽  
Halogen Bonds ◽  
Direct Transformation ◽  
Palladium Catalyzed

The direct transformation of unactivated C(sp3)–H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

2021 ◽  
Vol 57 (16) ◽  
pp. 2021-2024
Author(s):  
Zhi-Chao Qi ◽  
Qin-Xin Lou ◽  
Yuan Niu ◽  
Shang-Dong Yang
Keyword(s):  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Yang Wu ◽  
Feng Jin ◽  
Bao Xiaoguang ◽  
Ji-Bao Xia
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalysis ◽  
Computational Studies ◽  
Organic Azides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Synthesis ◽  
2021 ◽  
Author(s):  
Santanu Ghora ◽  
Chinnabattigalla Sreenivasulu ◽  
Gedu Satyanarayana
Keyword(s):  
Functional Group ◽  
Exchange Process ◽  
Palladium Catalysis ◽  
Allylic Alcohols ◽  
Heck Coupling ◽  
One Pot ◽  
Synthetic Process ◽  
Intramolecular Condensation ◽  
The One

AbstractAn efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Palladium-catalyzed paraformaldehyde insertion: a three-component synthesis of benzofurans

2016 ◽  
Vol 14 (10) ◽  
pp. 2819-2823 ◽  
Author(s):  
Xiufang Cheng ◽  
Yi Peng ◽  
Jun Wu ◽  
Guo-Jun Deng
Keyword(s):  
Palladium Catalysis ◽  
Phenacyl Bromides ◽  
Palladium Catalyzed

2-Aroylbenzofurans were prepared from 2-bromophenols, phenacyl bromides and paraformaldehyde under palladium catalysis conditions.

scholarly journals Ester Dance Reaction on the Aromatic Ring

2019 ◽  
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero)arene systems, with the exception of halogen atoms in a halogen dance reaction. Herein, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero)aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic as well as state-of-the-art transformations including an amidation, acylations and decarbonylative couplings.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

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