Wenjun Lu

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Name: 陆文军; WenJun Lu

Organization: Shanghai Jiao Tong University , China

Department: Department of Chemistry

Title: Associate Professor(PhD)

TOPICS

Organic Chemistry

C-H Activation

Chemicals
References

Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C–H Bonds with NaCl/Oxone at Room Temperature

Co-reporter:Mengdi Zhao and Wenjun Lu

Organic Letters September 1, 2017 Volume 19(Issue 17) pp:

Publication Date(Web):August 17, 2017

DOI:10.1021/acs.orglett.7b02153

A visible light-induced monochlorination of cyclohexane with sodium chloride (5:1) has been successfully accomplished to afford chlorocyclohexane in excellent yield by using Oxone as the oxidant in H2O/CF3CH2OH at room temperature. Other secondary and primary alkyl sp3 C–H bonds of cycloalkanes and functional branch/linear alkanes can also be chlorinated, respectively, under similar conditions. The selection of a suitable organic solvent is crucial in these efficient radical chlorinations of alkanes in two-phase solutions. It is studied further by the achievement of high chemoselectivity in the chlorination of the benzyl sp3 C–H bond or the aryl sp2 C–H bond of toluene.

Palladium-Catalyzed β-Mesylation of Simple Amide via Primary sp3 C–H Activation

Co-reporter:Ren Zhao and Wenjun Lu

Organic Letters April 7, 2017 Volume 19(Issue 7) pp:

Publication Date(Web):March 22, 2017

DOI:10.1021/acs.orglett.7b00536

A β-mesylation of primary sp3 C–H bonds from simple amides with methanesulfonic anhydride (Ms2O) has been established successfully at 80 °C in a Pd(OAc)2 (catalyst)/K2S2O8 (oxidant)/CF3CH2OH (solvent) system. These amide substrates involve N-monosubstituted linear, branch, or cyclic alkanes, and electron-deficient benzyl compounds. The β-mesylated amide products can be converted easily to β-fluoroamides or β-lactams through inter- or intramolecular SN2 processes.

Palladium-Catalyzed β-Acyloxylation of Simple Amide via sp3 C–H Activation

Co-reporter:Lihong Zhou and Wenjun Lu

Organic Letters 2014 Volume 16(Issue 2) pp:508-511

Publication Date(Web):December 27, 2013

DOI:10.1021/ol403393w

β-Acyloxy amides are prepared in moderate to high yields by palladium-catalyzed acyloxylation of primary sp3 C–H bonds from simple amides without any special directing group. A catalytic system of Pd(OAc)2/CF3CO2H/K2S2O8 is available to various amides with N-substituted by linear alkanes, cyclic alkanes, and electron-deficient benzyl compounds in this reaction. Acyloxylated products could be transformed easily to the corresponding β-hydroxy amides.

Towards Ideal Synthesis: Alkenylation of Aryl CH Bonds by a FujiwaraMoritani Reaction

Co-reporter:Lihong Zhou ;Dr. Wenjun Lu

Chemistry - A European Journal 2014 Volume 20( Issue 3) pp:634-642

Publication Date(Web):

DOI:10.1002/chem.201303670

Abstract

An overview of recent progress in the Fujiwara–Moritani reaction, which is the palladium-catalyzed oxidative coupling of arenes with olefins to afford alkenyl arenes, is described. It is emphasized that regioselectivity on aryl ortho- or meta-CH activation could be controlled very well in the presence of Pd, Rh, or Ru catalysts with the assistance of various chelation groups on aromatic rings in this coupling reaction. Catalytic alkenylation of aryl CH bonds from simple arenes is also discussed, especially from electron-deficient arenes. These advanced protocols would not only make the Fujiwara–Moritani reaction more useful and applicable in organic synthesis but also light the way for the further development of the functionalization of normal CH bonds.

Palladium(II)-Catalyzed Coupling of Electron-Deficient Arenes via C–H Activation

Co-reporter:Lihong Zhou and Wenjun Lu

Organometallics 2012 Volume 31(Issue 6) pp:2124-2127

Publication Date(Web):March 9, 2012

DOI:10.1021/om300114e

Homocoupling and cross-coupling of electron-deficient arenes, including nitrobenzene, (trifluoromethyl)benzene, ethyl benzoate, etc., have been developed to afford biaryls using a catalytic system of Pd(OAc)2/trifluoroacetic acid (TFA)/O2 or K2S2O8. The crucial step is to tune the concentrations of arenes and the loading of TFA carefully to enhance the reaction rates and the selectivity of these couplings involving dual C–H activation.