FeiJie Song - Cochemist

Gold-catalyzed cascade C–H/C–H cross-coupling/cyclization/alkynylation: an efficient access to 3-alkynylpyrroles

Co-reporter:Shuai Zhang, Yuanhong Ma, Jingbo Lan, Feijie Song and Jingsong You

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 21) pp:5867-5870

Publication Date(Web):16 Apr 2015

DOI:10.1039/C5OB00599J

An efficient approach to 3-alkynylpyrroles has been developed through the gold-catalyzed reaction of β-enamino derivatives with terminal alkynes, which features complete regiocontrol, relatively wide substrate scope, and high functional group tolerance. Mechanistic studies show that the reaction proceeds through the gold-catalyzed cascade oxidative C–H/C–H cross-coupling, cyclization and alkynylation.

Versatile palladium-catalyzed C–H olefination of (hetero)arenes at room temperature

Co-reporter:Zhijie She, Yang Shi, Yumin Huang, Yangyang Cheng, Feijie Song and Jingsong You

Chemical Communications 2014 vol. 50(Issue 90) pp:13914-13916

Publication Date(Web):17 Sep 2014

DOI:10.1039/C4CC05827E

The room-temperature oxidative C–H/C–H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2 and TFA, as the catalyst and cheap (NH4)2S2O8 as the oxidant under air.

Silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines: highly efficient synthesis of structurally diverse fluorinated indole derivatives

Co-reporter:Lei Yang, Yuanhong Ma, Feijie Song and Jingsong You

Chemical Communications 2014 vol. 50(Issue 23) pp:3024-3026

Publication Date(Web):28 Jan 2014

DOI:10.1039/C3CC49851D

Highly efficient approaches to obtain structurally diverse fluorinated indole derivatives have been realized through the Ag-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines in the presence of NFSI or Selectfluor.

Gold-Catalyzed C(sp3)H/C(sp)H Coupling/Cyclization/Oxidative Alkynylation Sequence: A Powerful Strategy for the Synthesis of 3-Alkynyl Polysubstituted Furans

Co-reporter:Yuanhong Ma;Shuai Zhang;Shiping Yang;Dr. Feijie Song;Dr. Jingsong You

Angewandte Chemie 2014 Volume 126( Issue 30) pp:8004-8008

Publication Date(Web):

DOI:10.1002/ange.201402475

Abstract

In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially CH/CH cross-coupling have been under represented. By taking advantage of the unique redox property and carbophilic π acidity of gold, this work realizes the first gold-catalyzed direct C(sp³)H alkynylation of 1,3-dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region-defined approach to 3-alkynyl polysubstituted furans.

Gold-Catalyzed C(sp3)H/C(sp)H Coupling/Cyclization/Oxidative Alkynylation Sequence: A Powerful Strategy for the Synthesis of 3-Alkynyl Polysubstituted Furans

Co-reporter:Yuanhong Ma;Shuai Zhang;Shiping Yang;Dr. Feijie Song;Dr. Jingsong You

Angewandte Chemie International Edition 2014 Volume 53( Issue 30) pp:7870-7874

Publication Date(Web):

DOI:10.1002/anie.201402475

Abstract

In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially CH/CH cross-coupling have been under represented. By taking advantage of the unique redox property and carbophilic π acidity of gold, this work realizes the first gold-catalyzed direct C(sp³)H alkynylation of 1,3-dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region-defined approach to 3-alkynyl polysubstituted furans.

Aerobic Ru-catalyzed direct C2-olefination of N-heteroarenes with alkenes directed by a removable N-dimethylcarbamoyl group

Co-reporter:Luo-Qiang Zhang, Shiping Yang, Xiaolei Huang, Jingsong You and Feijie Song

Chemical Communications 2013 vol. 49(Issue 78) pp:8830-8832

Publication Date(Web):31 Jul 2013

DOI:10.1039/C3CC44787A

A highly efficient and selective Ru-catalyzed direct C2-olefination of indoles, pyrroles, and carbazoles assisted by a removable N-dimethylcarbamoyl group has been developed by using O2 as the terminal oxidant. Both electron-deficient and unactivated alkenes are applicable to the protocol.

One-step synthesis of imidazoline-containing macrocycles and their complexation with fullerenes C60 and C70

Co-reporter:Fan Yang, Zhigang Wang, Feijie Song, Xingyan Liu, Jingbo Lan and Jingsong You

Chemical Communications 2013 vol. 49(Issue 53) pp:5975-5977

Publication Date(Web):14 May 2013

DOI:10.1039/C3CC42640H

A new family of imidazoline–arylene macrocycles have been constructed through the simultaneous formation of four imidazoline rings in one step. These macrocycles can efficiently complex with fullerenes C60 and C70 through the formation of ground-state complexes.

Tandem oxidation–oxidative C–H/C–H cross-coupling: synthesis of arylquinones from hydroquinones

Co-reporter:Shuai Zhang, Feijie Song, Dongbing Zhao and Jingsong You

Chemical Communications 2013 vol. 49(Issue 40) pp:4558-4560

Publication Date(Web):26 Mar 2013

DOI:10.1039/C3CC41067F

A concise and efficient approach to arylquinones from widely available hydroquinones has been developed through a tandem reaction involving the oxidation of hydroquinones and subsequent oxidative C–H/C–H cross-coupling of the resulting quinones with arenes.

Palladium-catalyzed C–H activation of anilides at room temperature: ortho-arylation and acetoxylation

Co-reporter:Fan Yang, Feijie Song, Wei Li, Jingbo Lan and Jingsong You

RSC Advances 2013 vol. 3(Issue 25) pp:9649-9652

Publication Date(Web):29 Apr 2013

DOI:10.1039/C3RA41981A

Room-temperature ortho-arylation and acetoxylation of anilides have been achieved using cationic palladium (Pd[TFA]+) as catalyst and (NH4)2S2O8 as oxidant. Preliminary investigation of the mechanism suggests that palladium may have different oxidation states in the catalytic cycles of these two transformations.

Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones

Co-reporter:Yuanhong Ma;Dr. Jingsong You;Dr. Feijie Song

Chemistry - A European Journal 2013 Volume 19( Issue 4) pp:1189-1193

Publication Date(Web):

DOI:10.1002/chem.201203354

One-step synthesis of imidazoline-containing macrocycles and their complexation with fullerenes C60 and C70

Co-reporter:Fan Yang, Zhigang Wang, Feijie Song, Xingyan Liu, Jingbo Lan and Jingsong You

Chemical Communications 2013 - vol. 49(Issue 53) pp:NaN5977-5977

Publication Date(Web):2013/05/14

DOI:10.1039/C3CC42640H

A new family of imidazoline–arylene macrocycles have been constructed through the simultaneous formation of four imidazoline rings in one step. These macrocycles can efficiently complex with fullerenes C60 and C70 through the formation of ground-state complexes.

Silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines: highly efficient synthesis of structurally diverse fluorinated indole derivatives

Co-reporter:Lei Yang, Yuanhong Ma, Feijie Song and Jingsong You

Chemical Communications 2014 - vol. 50(Issue 23) pp:NaN3026-3026

Publication Date(Web):2014/01/28

DOI:10.1039/C3CC49851D

Highly efficient approaches to obtain structurally diverse fluorinated indole derivatives have been realized through the Ag-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines in the presence of NFSI or Selectfluor.

Versatile palladium-catalyzed C–H olefination of (hetero)arenes at room temperature

Co-reporter:Zhijie She, Yang Shi, Yumin Huang, Yangyang Cheng, Feijie Song and Jingsong You

Chemical Communications 2014 - vol. 50(Issue 90) pp:NaN13916-13916

Publication Date(Web):2014/09/17

DOI:10.1039/C4CC05827E

The room-temperature oxidative C–H/C–H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2 and TFA, as the catalyst and cheap (NH4)2S2O8 as the oxidant under air.

Tandem oxidation–oxidative C–H/C–H cross-coupling: synthesis of arylquinones from hydroquinones

Co-reporter:Shuai Zhang, Feijie Song, Dongbing Zhao and Jingsong You

Chemical Communications 2013 - vol. 49(Issue 40) pp:NaN4560-4560

Publication Date(Web):2013/03/26

DOI:10.1039/C3CC41067F

A concise and efficient approach to arylquinones from widely available hydroquinones has been developed through a tandem reaction involving the oxidation of hydroquinones and subsequent oxidative C–H/C–H cross-coupling of the resulting quinones with arenes.

Gold-catalyzed cascade C–H/C–H cross-coupling/cyclization/alkynylation: an efficient access to 3-alkynylpyrroles

Co-reporter:Shuai Zhang, Yuanhong Ma, Jingbo Lan, Feijie Song and Jingsong You

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 21) pp:NaN5870-5870

Publication Date(Web):2015/04/16

DOI:10.1039/C5OB00599J

An efficient approach to 3-alkynylpyrroles has been developed through the gold-catalyzed reaction of β-enamino derivatives with terminal alkynes, which features complete regiocontrol, relatively wide substrate scope, and high functional group tolerance. Mechanistic studies show that the reaction proceeds through the gold-catalyzed cascade oxidative C–H/C–H cross-coupling, cyclization and alkynylation.

Aerobic Ru-catalyzed direct C2-olefination of N-heteroarenes with alkenes directed by a removable N-dimethylcarbamoyl group

Co-reporter:Luo-Qiang Zhang, Shiping Yang, Xiaolei Huang, Jingsong You and Feijie Song

Chemical Communications 2013 - vol. 49(Issue 78) pp:NaN8832-8832

Publication Date(Web):2013/07/31

DOI:10.1039/C3CC44787A

A highly efficient and selective Ru-catalyzed direct C2-olefination of indoles, pyrroles, and carbazoles assisted by a removable N-dimethylcarbamoyl group has been developed by using O2 as the terminal oxidant. Both electron-deficient and unactivated alkenes are applicable to the protocol.