HongJun Ren

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Name: 任红军; HongJun Ren
Organization: Zhejiang Sci-Tech University
Department: Department of Chemistry
Title: Professor

TOPICS

Co-reporter:Shiru Yuan, Yuchen Luo, Jingyi Peng, Maozhong Miao, Jianfeng Xu, and Hongjun Ren
Organic Letters November 17, 2017 Volume 19(Issue 22) pp:6100-6100
Publication Date(Web):November 2, 2017
DOI:10.1021/acs.orglett.7b02948
An efficient asymmetric [2 + 3] annulation of simple aldehydes with N,N′-cyclic azomethine imines via oxidative N-heterocyclic carbene (NHC) catalysis is disclosed, affording bicyclic pyrazolidinones bearing two vicinal tertiary stereogenic centers with moderate to good yields (56–84% for 19 examples), good to excellent diastereoselectivities (>20:1 for 17 examples), and good to excellent enantioselectivities (66–98% for 19 examples). This direct α-carbon functionalization reaction of aldehyde can be readily performed on gram scale under mild conditions, and a five-membered transition state is proposed to rationalize the stereochemical outcome.
Co-reporter:Maozhong Miao, Yi Luo, Huaping Xu, Mengchao Jin, Zhengkai Chen, Jianfeng Xu, and Hongjun Ren
The Journal of Organic Chemistry December 1, 2017 Volume 82(Issue 23) pp:12224-12224
Publication Date(Web):October 23, 2017
DOI:10.1021/acs.joc.7b02087
The tunable nucleophilic nitration of 3-cyclopropylideneprop-2-en-1-ones with cheap sodium nitrite is described. This transformation proceeds with the assistance of a strained cyclopropane ring and allows for a divergent route to various synthetically useful β,γ-dinitro or γ-mononitro adducts in high yields with exclusive regio- and stereoselectivity. Additionally, a wide array of valuable functionalized N-unprotected pyrroles is achieved from the resulting β,γ-dinitro compounds via reductive cyclization strategy.
Co-reporter:Maozhong Miao;Huaping Xu;Yi Luo;Mengchao Jin;Zhengkai Chen;Jianfeng Xu
Organic Chemistry Frontiers 2017 vol. 4(Issue 9) pp:1824-1828
Publication Date(Web):2017/08/22
DOI:10.1039/C7QO00362E
A highly efficient conjugate addition and 5-endo-trig cyclization reaction of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates in the presence of iodine is described. A wide variety of densely functionalized 3-sulfonylfurans are furnished by single-step and one-pot methods, respectively. The results of such postcyclization modifications are also presented.
Co-reporter:Jianfeng Xu;Shiru Yuan;Jingyi Peng;Maozhong Miao;Zhengkai Chen
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 36) pp:7513-7517
Publication Date(Web):2017/09/20
DOI:10.1039/C7OB01783A
An efficient [4 + 3] annulation of 2-(1-tosylalkyl)phenols with C,N-cyclic azomethine imines via in situ generation of ortho-quinone methides (o-QMs) under mild basic reaction conditions is disclosed, furnishing biologically interesting seven-membered heterocyclic compounds with moderate to good yields and excellent diastereoselectivities. A gram-scale reaction is performed to demonstrate the potential in industrial application and two transition states are proposed to rationalize the outstanding diastereoselectivity.
Co-reporter:Jianfeng Xu;Shiru Yuan;Jingyi Peng;Maozhong Miao;Zhengkai Chen
Chemical Communications 2017 vol. 53(Issue 24) pp:3430-3433
Publication Date(Web):2017/03/21
DOI:10.1039/C7CC01232B
An asymmetric [2+2] annulation reaction through direct α-carbon functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis is disclosed. These in situ generated triazolium enolate intermediates undergo a highly stereoselective Mannich reaction with isatin-derived ketimines followed by intramolecular lactamization to afford enantioenriched spirooxindole β-lactams bearing two vicinal stereogenic centers.
Co-reporter:Zhengkai Chen, Hongli Li, Weipeng Dong, Maozhong Miao, and Hongjun Ren
Organic Letters 2016 Volume 18(Issue 6) pp:1334-1337
Publication Date(Web):February 25, 2016
DOI:10.1021/acs.orglett.6b00277
A general and expeditious approach for the metal-free mediated synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from hydrazones and aliphatic amines has been achieved under aerobic oxidative conditions. The reaction proceeds through a cascade C–H functionalization, double C–N bonds formation, and oxidative aromatization sequence.
Co-reporter:Maozhong Miao, Yi Luo, Huaping Xu, Zhengkai Chen, Jianfeng Xu, and Hongjun Ren
Organic Letters 2016 Volume 18(Issue 17) pp:4292-4295
Publication Date(Web):August 16, 2016
DOI:10.1021/acs.orglett.6b02047
An interesting and tunable hydrosulfonylation of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and acetic acid is described. The corresponding β- or γ-addition products can be produced in good to excellent yields with high selectivities, respectively. A rationale for these transformations is proposed base on the controlled experiments.
Co-reporter:Maozhong Miao, Yi Luo, Hongli Li, Xin Xu, Zhengkai Chen, Jianfeng Xu, and Hongjun Ren
The Journal of Organic Chemistry 2016 Volume 81(Issue 12) pp:5228-5235
Publication Date(Web):May 25, 2016
DOI:10.1021/acs.joc.6b00734
Lewis acid catalyzed directly dehydrative carbon–carbon bond formation reaction of 2-furylcarbinols with β-keto amides provides a straightforward method for regioselective synthesis of (Z)-furyl enols. Moreover, this Lewis acid catalyzed cross-coupling reaction can be extended to an interesting heterocyclic version featuring a functionalized 3-furyl-4-hydroxycoumarin synthesis.
Co-reporter:Lijun Xu, Zhubo Liu, Weipeng Dong, Jinyu Song, Maozhong Miao, Jianfeng Xu and Hongjun Ren  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 22) pp:6333-6337
Publication Date(Web):29 Apr 2015
DOI:10.1039/C5OB00594A
A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for multiple synthetic applications. The α- and γ-isomers can be converted to the corresponding 3H-indole and indole derivatives in multigram scale respectively.
Co-reporter:Maozhong Miao;Xin Xu;Lijun Xu
European Journal of Organic Chemistry 2014 Volume 2014( Issue 27) pp:5896-5900
Publication Date(Web):
DOI:10.1002/ejoc.201402823

Abstract

Electrophilic cyclization of cyclopropylideneallenyl ketones in the presence of I2/CuI offers an efficient and straightforward route to highly substituted furans under mild reaction conditions. Further transformation of the resulting iodofurans provides structurally more advanced furan derivatives.

Co-reporter:Lijun Xu, Weijun Yang, Lili Zhang, Maozhong Miao, Zhigen Yang, Xin Xu, and Hongjun Ren
The Journal of Organic Chemistry 2014 Volume 79(Issue 19) pp:9206-9221
Publication Date(Web):September 2, 2014
DOI:10.1021/jo501640d
The efficient synthesis of fluorenes from biaryl triazenes is successfully developed. Up to 27 examples of biaryl triazenes are converted into their corresponding fluorene derivatives in the presence of CF3COOH (4.0 equiv). Mechanism research indicates that the reaction undergoes concerted processes, and pentacoordinate carbocations may be involved in these reactions.
Co-reporter:Weijun Yang, Lijun Xu, Zhengkai Chen, Lili Zhang, Maozhong Miao, and Hongjun Ren
Organic Letters 2013 Volume 15(Issue 6) pp:1282-1285
Publication Date(Web):February 22, 2013
DOI:10.1021/ol400223d
An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction–cyclization–rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H2 (1 atm) in the presence of Pd/C, 4-quinolones were obtained in excellent yields.
Co-reporter:Zhengkai Chen;Weijun Yang;Lijun Xu;Lili Zhang;Maozhong Miao
European Journal of Organic Chemistry 2013 Volume 2013( Issue 32) pp:7411-7420
Publication Date(Web):
DOI:10.1002/ejoc.201300966

Abstract

A transition-metal-free tandem O-arylation/hydroxylation approach has been developed for the efficient synthesis of highly substituted 2-hydroxyflavanones from triazenylaryl-substituted diketones. The intermediate benzopyrylium cation may be involved in these reactions.

Co-reporter:Xiaobo Shang;Lijun Xu;Weijun Yang;Jun Zhou;Maozhong Miao
European Journal of Organic Chemistry 2013 Volume 2013( Issue 24) pp:5475-5484
Publication Date(Web):
DOI:10.1002/ejoc.201300660

Abstract

A simple and highly efficient reaction promoted by Lewis acid has been demonstrated for the synthesis of dibenzopyranones. The metal-free annulation can tolerate a series of functional groups and also allows the synthesis of coumarins and phenanthridinones in good to excellent yields.

Co-reporter:Weijun Yang;Zhigen Yang;Lijun Xu;Lili Zhang;Xin Xu;Dr. Maozhong Miao ;Dr. Hongjun Ren
Angewandte Chemie 2013 Volume 125( Issue 52) pp:14385-14389
Publication Date(Web):
DOI:10.1002/ange.201306632
Co-reporter:Weijun Yang;Zhigen Yang;Lijun Xu;Lili Zhang;Xin Xu;Dr. Maozhong Miao ;Dr. Hongjun Ren
Angewandte Chemie International Edition 2013 Volume 52( Issue 52) pp:14135-14139
Publication Date(Web):
DOI:10.1002/anie.201306632
Co-reporter:Guoqing Zhao;Binjie Wang;Weijun Yang
European Journal of Organic Chemistry 2012 Volume 2012( Issue 31) pp:6236-6247
Publication Date(Web):
DOI:10.1002/ejoc.201200902

Abstract

A Lewis-acid-promoted approach to the synthesis of highly functionalized dihydrobenzofuran derivatives was developed. A diverse range of functional groups are tolerated in this type of reaction. The reaction mechanism investigation indicates that the highly reactive phenyl cation intermediate is probably involved in this process. The chirality of substrate is retained under the reaction conditions.

Co-reporter:Jun Zhou;Weijun Yang;Binjie Wang;Dr. Hongjun Ren
Angewandte Chemie 2012 Volume 124( Issue 49) pp:
Publication Date(Web):
DOI:10.1002/ange.201206578
Co-reporter:Jun Zhou;Weijun Yang;Binjie Wang;Dr. Hongjun Ren
Angewandte Chemie International Edition 2012 Volume 51( Issue 49) pp:
Publication Date(Web):
DOI:10.1002/anie.201206578
Co-reporter:Lijun Xu, Zhubo Liu, Weipeng Dong, Jinyu Song, Maozhong Miao, Jianfeng Xu and Hongjun Ren
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 22) pp:NaN6337-6337
Publication Date(Web):2015/04/29
DOI:10.1039/C5OB00594A
A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for multiple synthetic applications. The α- and γ-isomers can be converted to the corresponding 3H-indole and indole derivatives in multigram scale respectively.
Co-reporter:Jianfeng Xu, Shiru Yuan, Jingyi Peng, Maozhong Miao, Zhengkai Chen and Hongjun Ren
Chemical Communications 2017 - vol. 53(Issue 24) pp:NaN3433-3433
Publication Date(Web):2017/03/06
DOI:10.1039/C7CC01232B
An asymmetric [2+2] annulation reaction through direct α-carbon functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis is disclosed. These in situ generated triazolium enolate intermediates undergo a highly stereoselective Mannich reaction with isatin-derived ketimines followed by intramolecular lactamization to afford enantioenriched spirooxindole β-lactams bearing two vicinal stereogenic centers.
N-(4-fluorobenzyl)-2-iodoaniline
N-(3-fluorobenzyl)-2-iodoaniline
(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Tetrafluoroborate
Benzenamine, 2-iodo-6-methyl-
Benzenemethanamine, N-(2-iodophenyl)-4-nitro-
Benzenamine, 4-(1,1-dimethylethyl)-2-iodo-
2-(1-ETHYLPENTYL) BENZIMIDAZOLE
2-Furanmethanol, α-methyl-α-phenyl-
1H-BENZIMIDAZOLE, 2-PHENYL-5-(TRIFLUOROMETHYL)-