Luo Yang

Find an error

Name:

Organization: Xiangtan University

Department: Key Laboratory for Environmentally Friendly Chemistry and Application, Department of Chemistry

Title:

TOPICS

Organic Chemistry

Amination

Chemicals
References

Metal-free decarbonylative alkylation–aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide

Co-reporter:Yu-Xia Li;Qi-Qiang Wang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 6) pp:1338-1342

Publication Date(Web):2017/02/07

DOI:10.1039/C7OB00030H

A convenient metal-free decarbonylative alkylation–aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide (NHPI) to yield phthalimide protected alkoxyamines is developed. With DTBP as an oxidant and radical-initiator, this reaction smoothly converts aliphatic aldehydes into alkyl radicals and subsequently allows the cascade construction of C(sp3)–C(sp3) and C(sp3)–O bonds via radical–radical coupling.

Fe-Catalyzed radical-type difunctionalization of styrenes with aliphatic aldehydes and trimethylsilyl azide via a decarbonylative alkylation–azidation cascade

Co-reporter:Wei-Yu Li;Qi-Qiang Wang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 47) pp:9987-9991

Publication Date(Web):2017/12/06

DOI:10.1039/C7OB02598J

A convenient Fe-catalyzed decarbonylative alkylation–azidation cascade reaction of styrene derivatives with aliphatic aldehydes and TMSN3 to provide aliphatic azides is developed. With DTBP as an oxidant and radical initiator, this reaction smoothly converts aliphatic aldehydes into 1°, 2° and 3° alkyl radicals and subsequently allows for the cascade construction of C(sp3)–C(sp3) and C(sp3)–N bonds via radical insertion and nucleophilic azidation.

Iodine-catalyzed oxidative multiple C–H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones

Co-reporter:Di Zhu;Wen-Kun Luo;Da-You Ma

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 34) pp:7112-7116

Publication Date(Web):2017/08/30

DOI:10.1039/C7OB01539A

An iodine-catalyzed multiple C–H bond functionalization of isoquinolines with methylarenes via a successive benzylic sp3 C–H iodination/N-benzylation/amidation/double sp2 C–H oxidation sequence is developed. This reaction utilizes un-functionalized isoquinolines and readily available methylarenes as starting materials, proceeds under metal-free conditions, and avoids a multi-step experimental operation, to make it an efficient and practical method for the synthesis of N-benzyl isoquinoline-1,3,4-triones.

Iodine-Catalyzed Oxidative Functionalization of Azaarenes with Benzylic C(sp3)–H Bonds via N-Alkylation/Amidation Cascade: Two-Step Synthesis of Isoindolo[2,1-b]isoquinolin-7(5H)-one

Co-reporter:Wen-Kun Luo, Xin Shi, Wang Zhou, and Luo Yang

Organic Letters 2016 Volume 18(Issue 9) pp:2036-2039

Publication Date(Web):April 28, 2016

DOI:10.1021/acs.orglett.6b00646

An efficient and practical iodine-catalyzed oxidative functionalization of azaarenes with benzylic C–H bonds via an N-alkylation and amidation cascade is developed to provide isoquinolin-1(2H)-ones. This method utilizes readily available unfunctionalized azaarenes and methylarenes as starting materials and proceeds under metal-free conditions with good to excellent yields, avoiding the use of expensive noble metal catalysts and generation of halide and metal wastes. The synthetic utility of this reaction is exemplified by the concise, two-step synthesis of isoindolo[2,1-b]isoquinolin-7(5H)-one.

Metal-free synthesis of quinazolinones without any additives in water

Co-reporter:Ben-Quan Hu, Jie Cui, Li-Xia Wang, Ya-Lin Tang and Luo Yang

RSC Advances 2016 vol. 6(Issue 50) pp:43950-43953

Publication Date(Web):20 Apr 2016

DOI:10.1039/C6RA05777B

Here we report that an excess amount of aldehyde, in particular, aliphatic aldehyde, without any additives, efficiently facilitates the oxidation of aminal intermediates to quinazolinones in pure water.

Iodine-Catalyzed Oxidative Benzylic CH Bond Amination of Azaarenes: Practical Synthesis of Quinazolin-4(3H)-ones

Co-reporter:Dr. Luo Yang;Xin Shi;Ben-Quan Hu;Dr. Li-Xia Wang

Asian Journal of Organic Chemistry 2016 Volume 5( Issue 4) pp:494-498

Publication Date(Web):

DOI:10.1002/ajoc.201600041

Abstract

An efficient iodine-catalyzed oxidative benzylic C−H bond amination of azaarenes to afford 2-heteroaryl quinazolinones has been developed. This reaction utilizes unfunctionalized alkyl azaarenes as starting materials and proceeds under metal-free conditions with dioxygen as the terminal oxidant, thus is much “greener” than the previous synthetic methods.

Pd-catalyzed chemo- and regioselective cross-coupling of two enamides

Co-reporter:Hong-Mei Liu, Wen Lu, Cui-Ping Luo, Luo Yang

Tetrahedron Letters 2016 Volume 57(Issue 37) pp:4243-4245

Publication Date(Web):14 September 2016

DOI:10.1016/j.tetlet.2016.08.026

•Palladium-catalyzed head-to-tail cross-coupling of enamides.•Excellent chemo-/regioselective are realized.•Up to 20 examples and 93% yield.A convenient Pd-catalyzed cross-coupling of two different enamides is developed to afford the head-to-tail heterodimerization products predominately in (Z)-configuration and up to 93% yield, with good chemo- and regioselectivity.

Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls

Co-reporter:Ren-Jin Tang, Qing He and Luo Yang

Chemical Communications 2015 vol. 51(Issue 27) pp:5925-5928

Publication Date(Web):24 Feb 2015

DOI:10.1039/C4CC10155C

A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis.

Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles

Co-reporter:Ren-Jin Tang;Lei Kang

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 9) pp:2055-2060

Publication Date(Web):

DOI:10.1002/adsc.201500268

Rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes

Co-reporter:Lei Kang, Feng Zhang, Lin-Ting Ding and Luo Yang

RSC Advances 2015 vol. 5(Issue 122) pp:100452-100456

Publication Date(Web):16 Nov 2015

DOI:10.1039/C5RA21610A

A rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.

A copper-catalyzed domino reaction to construct functionalized indolizinones

Co-reporter:Ben-Quan Hu, Li-Xia Wang, Gang Shen, Ya-Lin Tang and Luo Yang

RSC Advances 2015 vol. 5(Issue 121) pp:100097-100101

Publication Date(Web):09 Nov 2015

DOI:10.1039/C5RA20119E

An efficient copper-catalyzed domino reaction to 3,8a-disubstituted indolizinones has been firstly developed, and the protocol uses pyridine ketones and terminal alkynes as the starting materials, overriding the isolation of propargylic alcohols.

C(sp3)–C(sp3) bond formation via copper/Brønsted acid co-catalyzed C(sp3)–H bond oxidative cross-dehydrogenative-coupling (CDC) of azaarenes

Co-reporter:Fang-Fang Wang, Cui-Ping Luo, Guojun Deng and Luo Yang

Green Chemistry 2014 vol. 16(Issue 5) pp:2428-2431

Publication Date(Web):31 Jan 2014

DOI:10.1039/C4GC00038B

A copper/Brønsted acid dual-catalyst promoted oxidative cross-dehydrogenative-coupling of alkylazaarenes and tertiary amines for C(sp3)–C(sp3) bond formation was developed. This method uses dioxygen as the terminal oxidant under mild reaction conditions and would provide a convenient benzylic C–H transformation of alkylazaarenes to biologically active pharmaceutics.

Brønsted Acid Catalyzed Benzylic C–H Bond Functionalization of Azaarenes: Nucleophilic Addition to Nitroso Compounds

Co-reporter:Xu Gao, Feng Zhang, Guojun Deng, and Luo Yang

Organic Letters 2014 Volume 16(Issue 14) pp:3664-3667

Publication Date(Web):July 1, 2014

DOI:10.1021/ol501422k

A practical Brønsted acid promoted benzylic C–H functionalization of 2-alkylazaarenes and nucleophilic addition to nitroso compounds was developed under mild conditions. Switched by Brønsted acids, this method can afford azaarene-2-aldimines, azaarene-2-carbaldehyde, or azaarene-2-oximes selectively. No metal, base, oxidant, or other additives were required.

Silver-mediated oxidative vinylic C–H bond sulfenylation of enamides with disulfides

Co-reporter:Luo Yang, Qing Wen, Fuhong Xiao and Guo-Jun Deng

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 47) pp:9519-9523

Publication Date(Web):15 Oct 2014

DOI:10.1039/C4OB01970A

A silver-mediated oxidative vinylic C–H bond sulfenylation of enamides was developed. This method is compatible with diaryl and dialkyl disulfides to deliver biologically precious chalcogenated olefins efficiently. A plausible non-chain radical mechanism was proposed for understanding this novel sulfenylation based on the mechanistic studies.

Rhodium(III)-Catalyzed C(sp2)H Activation and Electrophilic Amidation with N-Fluorobenzenesulfonimide

Co-reporter:Ren-Jin Tang;Cui-Ping Luo;Chao-Jun Li

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 5) pp:869-873

Publication Date(Web):

DOI:10.1002/adsc.201201133

Abstract

An electrophilic amidation via a cationic rhodium(III)-catalyzed C(sp²)H activation has been developed with the commercially available N-fluorobenzenesulfonimide as the amino source under external oxidant-free conditions. This amidation requires only a catalytic amount of base and exhibits excellent functional group tolerance and regioselectivity, providing a new avenue in direct C(sp²)H amidation.

Transition Metal-Free Regioselective C-3 Amidation of Indoles with N-Fluorobenzenesulfonimide

Co-reporter:Hai-Hong Liu;Yi Wang;Guojun Deng

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 17) pp:3369-3374

Publication Date(Web):

DOI:10.1002/adsc.201300767

Brønsted acid promoted benzylic C–H bond functionalization of azaarenes: nucleophilic addition to aldehydes

Co-reporter:Fang-Fang Wang, Cui-Ping Luo, Yi Wang, Guojun Deng and Luo Yang

Organic & Biomolecular Chemistry 2012 vol. 10(Issue 43) pp:8605-8608

Publication Date(Web):13 Sep 2012

DOI:10.1039/C2OB26604K

A practical Brønsted acid promoted benzylic C–H functionalization of 2-methylazaarenes and nucleophilic addition to aldehydes was developed in good to excellent yields. A six-membered hydrogen-bonding transition state is proposed to be crucial for the reaction. Ready availability of the two starting materials, the use of acetic acid as the catalyst and the facile reaction conditions will guarantee this synthetic method attractive to the synthesis of bioactive pyridine and quinoline derivatives.

Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls

Co-reporter:Ren-Jin Tang, Qing He and Luo Yang

Chemical Communications 2015 - vol. 51(Issue 27) pp:NaN5928-5928

Publication Date(Web):2015/02/24

DOI:10.1039/C4CC10155C

Brønsted acid promoted benzylic C–H bond functionalization of azaarenes: nucleophilic addition to aldehydes

Co-reporter:Fang-Fang Wang, Cui-Ping Luo, Yi Wang, Guojun Deng and Luo Yang

Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 43) pp:NaN8608-8608

Publication Date(Web):2012/09/13

DOI:10.1039/C2OB26604K

Silver-mediated oxidative vinylic C–H bond sulfenylation of enamides with disulfides

Co-reporter:Luo Yang, Qing Wen, Fuhong Xiao and Guo-Jun Deng