Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water

We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.

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Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.183 ◽

2018 ◽

Vol 14 ◽

pp. 2090-2097 ◽

Cited By ~ 6

Author(s):

Jiao-Na Han ◽

Cong Du ◽

Xinju Zhu ◽

Zheng-Long Wang ◽

Yue Zhu ◽

...

Keyword(s):

Catalytic System ◽

Functional Group ◽

Secondary Alcohols ◽

Reaction Conditions ◽

Biologically Relevant ◽

Efficient Approach ◽

Directing Group ◽

Aryl Ethers

A cobalt-catalyzed C(sp2)–H alkoxylation of 1-naphthylamine derivatives has been disclosed, which represents an efficient approach to synthesize aryl ethers with broad functional group tolerance. It is noteworthy that secondary alcohols, such as hexafluoroisopropanol, isopropanol, isobutanol, and isopentanol, were well tolerated under the current catalytic system. Moreover, a series of biologically relevant fluorine-aryl ethers were easily obtained under mild reaction conditions after the removal of the directing group.

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Differentiation and Functionalization of Adjacent, Remote C–H Bonds

10.26434/chemrxiv.8156561 ◽

2019 ◽

Author(s):

Hang Shi ◽

Lu Yi ◽

Jiang Weng ◽

Katherine Bay ◽

Xiangyang Chen ◽

...

Keyword(s):

Catalytic System ◽

Functional Group ◽

Hydrocinnamic Acid ◽

Molecular Architectures ◽

Site Selective ◽

Developing Strategies

Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures1-4. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential4-6. In this context, distinguishing remote C–H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C–H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukemia agent, and hydrocinnamic acid substrates.

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Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

10.26434/chemrxiv.9978824.v1 ◽

2019 ◽

Author(s):

John Montgomery ◽

Alexander W. Rand

Keyword(s):

Catalytic System ◽

Functional Group ◽

Enantiomeric Excess ◽

New Method ◽

Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

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Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

10.26434/chemrxiv.9978824 ◽

2019 ◽

Author(s):

John Montgomery ◽

Alexander W. Rand

Keyword(s):

Catalytic System ◽

Functional Group ◽

Enantiomeric Excess ◽

New Method ◽

Aryl Bromides

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Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C–H activation of phthalazinones and allenes

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01458g ◽

2021 ◽

Vol 19 (35) ◽

pp. 7701-7705

Author(s):

Chuanliu Yin ◽

Tianshuo Zhong ◽

Xiangyun Zheng ◽

Lianghao Li ◽

Jian Zhou ◽

...

Keyword(s):

Catalytic System ◽

Functional Group ◽

Direct Synthesis ◽

Atom Economy

An Rh(iii)-catalyzed annulation of phthalazinones and various allenes was developed, leading to the formation of indazole derivatives. This catalytic system exhibits excellent functional group tolerance and atom economy.

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A Highly Efficient Catalytic System for Polycondensation of 2,7-Dibromo-9,9-dioctylfluorene and 1,2,4,5-Tetrafluorobenzene via Direct Arylation

Macromolecules ◽

10.1021/ma302558z ◽

2013 ◽

Vol 46 (2) ◽

pp. 370-374 ◽

Cited By ~ 113

Author(s):

Masayuki Wakioka ◽

Yutaro Kitano ◽

Fumiyuki Ozawa

Keyword(s):

Catalytic System ◽

Direct Arylation ◽

Highly Efficient

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Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.7.139 ◽

2011 ◽

Vol 7 ◽

pp. 1198-1204 ◽

Cited By ~ 13

Author(s):

Michel Chiarucci ◽

Mirko Locritani ◽

Gianpiero Cera ◽

Marco Bandini

Keyword(s):

Catalytic System ◽

Functional Group ◽

Direct Synthesis ◽

Catalytic Process ◽

Primary Alcohols

Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures.

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