Bing Han

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Name: 韩丙; Han, Bing

Organization: Lanzhou University , China

Department: College of Chemistry and Chemical Engineering

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1′H-Spiro[azirine-2,4′-quinolin]-2′(3′H)-ones

Co-reporter:Qiang Meng, Fei Chen, Wei Yu, and Bing Han

Organic Letters October 6, 2017 Volume 19(Issue 19) pp:

Publication Date(Web):September 21, 2017

DOI:10.1021/acs.orglett.7b02453

A novel method for the synthesis of trifluoromethyl-containing 1′H-spiro[azirine-2,4′-quinolin]-2′(3′H)-ones by a CF3-radical-triggered tandem reaction of benzene-linked 1,7-enynes is described. This protocol utilizes 1-trifluoromethyl-1,2-benziodoxole as the trifluoromethylating reagent and TMSN3 as the aminating reagent. By this method, various potentially bioactive trifluoromethylated 1′H-spiro[azirine-2,4′-quinolin]-2′(3′H)-ones were facilely synthesized via a radical cascade process.

Dioxygen Activation via Cu-Catalyzed Cascade Radical Reaction: An Approach to Isoxazoline/Cyclic Nitrone-Featured α-Ketols

Co-reporter:Xie-Xue Peng, Dian Wei, Wen-Jun Han, Fei Chen, Wei Yu, and Bing Han

ACS Catalysis November 3, 2017 Volume 7(Issue 11) pp:7830-7830

Publication Date(Web):October 17, 2017

DOI:10.1021/acscatal.7b03078

A facile, mild, and efficient dioxygen activation for the synthesis of isoxazoline/cyclic nitrone-featured α-ketols has been achieved by Cu-catalyzed trifunctionalization of internal unactivated alkynes of unsaturated ketoximes at room temperature. 18O isotope tracing and DFT calculation reveal that a cascade iminoxyl radical dichotomous 5-exo-dig cyclization/oxygen activation/peroxy radical 4-endo-trig cyclization process was involved in the reaction.Keywords: alkyne; copper catalysis; DFT calculation; dioxygen activation; iminoxyl radical; radical cyclization;

tert-Butyl nitrite-mediated vicinal sulfoximation of alkenes with sulfinic acids: a highly efficient approach toward α-sulfonyl ketoximes

Co-reporter:Fei Chen;Neng-Neng Zhou;Jun-Long Zhan;Wei Yu

Organic Chemistry Frontiers 2017 vol. 4(Issue 1) pp:135-139

Publication Date(Web):2016/12/20

DOI:10.1039/C6QO00535G

A novel vicinal sulfoximation of alkenes was achieved under mild and metal-free conditions by using readily available sulfinic acids as the sulfonating agent and tert-butyl nitrite (TBN) as the radical initiator and the oxime source. Various structurally important α-sulfonyl ketoximes can be prepared from unactivated as well as activated alkenes in high efficiency by utilizing this protocol.

Copper-Catalyzed Oxidative Oxyamination/Diamination of Internal Alkenes of Unsaturated Oximes with Simple Amines

Co-reporter:Rui-Hua Liu, Dian Wei, Bing Han, and Wei Yu

ACS Catalysis 2016 Volume 6(Issue 10) pp:6525

Publication Date(Web):August 29, 2016

DOI:10.1021/acscatal.6b02065

A convenient and versatile oxidative intra/intermolecular oxyamination and diamination of unactivated alkenes has been developed through copper-catalyzed radical reactions of β,γ- and γ,δ-unsaturated ketoximes with electron-rich aryl and aliphatic amines. These reactions were carried out by employing di-tert-butyl peroxide (DTBP) or air as the terminal oxidant, and a series of useful nitrogen-containing 4,5-dihydroisoxazoles and cyclic nitrones were formed.Keywords: alkene; Cu; diamination; iminoxyl radicals; oxyamination

tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles

Co-reporter:Fei Chen, Qiang Meng, Shang-Qing Han, and Bing Han

Organic Letters 2016 Volume 18(Issue 14) pp:3330-3333

Publication Date(Web):June 24, 2016

DOI:10.1021/acs.orglett.6b01427

A novel, efficient, and facile vicinal sulfonamination of alkynes by the reaction of accessible 2-alkynyl arylazides with sulfinic acids in the presence of tert-butyl hydroperoxide (TBHP) has been developed. This protocol utilizes sulfinic acids as the sulfonating reagent, azidos as the aminating reagent, and TBHP as the sulfonyl radical initiator. By using this protocol, a variety of potentially bioactive 3-sulfonylindoles were facilely synthesized via direct annulation.

TEMPO-Mediated Aza-Diels–Alder Reaction: Synthesis of Tetrahydropyridazines Using Ketohydrazones and Olefins

Co-reporter:Xiu-Long Yang, Xie-Xue Peng, Fei Chen, and Bing Han

Organic Letters 2016 Volume 18(Issue 9) pp:2070-2073

Publication Date(Web):April 27, 2016

DOI:10.1021/acs.orglett.6b00702

A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels–Alder reaction with olefins.

Cu-Catalyzed [3 + 3] Annulation for the Synthesis of Pyrimidines via β-C(sp3)–H Functionalization of Saturated Ketones

Co-reporter:Jun-Long Zhan, Meng-Wei Wu, Fei Chen, and Bing Han

The Journal of Organic Chemistry 2016 Volume 81(Issue 23) pp:11994-12000

Publication Date(Web):November 2, 2016

DOI:10.1021/acs.joc.6b02181

A novel, efficient, and facile approach for the synthesis of structurally important pyrimidines has been successfully developed by Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones. This method provides a new protocol for the synthesis of pyrimidines by a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization via direct β-C(sp3)–H functionalization of saturated ketones followed by annulation with amidines.

Synthesis of Isoxazoline/Cyclic Nitrone-Featured Methylenes Using Unsaturated Ketoximes: A Dual Role of TEMPO

Co-reporter:Fei Chen, Xiu-Long Yang, Zhi-Wei Wu, and Bing Han

The Journal of Organic Chemistry 2016 Volume 81(Issue 7) pp:3042-3050

Publication Date(Web):March 8, 2016

DOI:10.1021/acs.joc.6b00180

A novel, metal-free, and regioselective approach for the synthesis of isoxazoline/cyclic nitrone-featured methylenes has been developed by the reaction of readily accessible β,γ- and γ,δ-unsaturated ketoximes with TEMPO via tandem iminoxyl radical-promoted cyclization/TEMPO-mediated Cope-like elimination, respectively. This protocol utilizes commercially available TEMPO as the iminoxyl radical initiator as well as the β-hydrogen acceptor in the Cope-like elimination.

Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles

Co-reporter:Xiao-Yong Duan, Xiu-Long Yang, Pan-Pan Jia, Man Zhang, and Bing Han

Organic Letters 2015 Volume 17(Issue 24) pp:6022-6025

Publication Date(Web):December 7, 2015

DOI:10.1021/acs.orglett.5b03003

An efficient and practical tandem cyclization/addition/cyclization strategy is developed for the initial generated hydrazonyl radicals derived from the oxidation of β,γ-unsaturated hydrazones. By using this protocol, structurally novel pyrazoline-functionalized oxindoles are prepared by the reaction of easily accessible β,γ-unsaturated hydrazones with N-aryl acrylamides under the metal- and solvent-free conditions of DTBP (di-tert-butyl peroxide) via a tandem intra/intermolecular C–N/C–C/C–C bond formation.

Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes

Co-reporter:Xie-Xue Peng, Yun-Jing Deng, Xiu-Long Yang, Lin Zhang, Wei Yu, and Bing Han

Organic Letters 2014 Volume 16(Issue 17) pp:4650-4653

Publication Date(Web):August 25, 2014

DOI:10.1021/ol502258n

A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from β,γ- and γ,δ-unsaturated ketoximes, respectively.

Synthesis of Isoxazoline-Functionalized Phenanthridines via Iminoxyl Radical-Participated Cascade Sequence

Co-reporter:Xiu-Long Yang, Fei Chen, Neng-Neng Zhou, Wei Yu, and Bing Han

Organic Letters 2014 Volume 16(Issue 24) pp:6476-6479

Publication Date(Web):December 9, 2014

DOI:10.1021/ol503335k

Readily accessible β,γ-unsaturated ketoximes reacted with 2-arylphenylisonitriles under the conditions of t-BuOOH and n-Bu4NI to give isoxazoline functionalized phenanthridines via tandem intramolecular/intermolecular C–O/C–C/C–C bond formation. The reaction involves the initial generation of iminoxyl radicals from the oxidation of β,γ-unsaturated ketoximes by t-BuOOH and n-Bu4NI followed a cascade radical cyclization/addition/cyclization sequence.

Transition from Radicals to Radicals: Substituent-Tuned Cyclization of Hydrazonyl Radicals

Co-reporter:Xiao-Yong Duan;Neng-Neng Zhou;Dr. Ran Fang;Xiu-Long Yang;Dr. Wei Yu ;Dr. Bing Han

Angewandte Chemie 2014 Volume 126( Issue 12) pp:3222-3226

Publication Date(Web):

DOI:10.1002/ange.201309918

Abstract

Hydrazonyl radicals are known for their π-electronic structures; however, their σ-electronic structures have not been reported as yet. Herein, we show that readily accessible β,γ- and γ,δ-unsaturated N-trichloroacetyl and N-trifluoroacetyl hydrazones can be conveniently converted into hydrazonyl σ radicals, which subsequently undergo 5-exo-trig radical cyclization at the N¹ or N² atom to form pyrazolines and azomethine imines, respectively.

Transition from Radicals to Radicals: Substituent-Tuned Cyclization of Hydrazonyl Radicals

Co-reporter:Xiao-Yong Duan;Neng-Neng Zhou;Dr. Ran Fang;Xiu-Long Yang;Dr. Wei Yu ;Dr. Bing Han

Angewandte Chemie International Edition 2014 Volume 53( Issue 12) pp:3158-3162

Publication Date(Web):

DOI:10.1002/anie.201309918

Abstract

Hydrazone Radical Promoted Vicinal Difunctionalization of Alkenes and Trifunctionalization of Allyls: Synthesis of Pyrazolines and Tetrahydropyridazines

Co-reporter:Xiao-Yong Duan, Xiu-Long Yang, Ran Fang, Xie-Xue Peng, Wei Yu, and Bing Han

The Journal of Organic Chemistry 2013 Volume 78(Issue 21) pp:10692-10704

Publication Date(Web):September 24, 2013

DOI:10.1021/jo4016908

The intramolecular addition of hydrazone radicals to carbon–carbon double bonds was achieved by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or DIAD (diisopropyl azodicarboxylate) as the hydrazone radical initiator as well as the carbon radical scavenger. Consequently, alkenes were difunctionalized to afford pyrazolines and tetrahydropyridazines via C–N forming 5-exo-trig and 6-exo-trig cyclizations, respectively, and allyls were trifunctionalized to afford pyrazolines via C–N forming tandem 1,5-H-shift/5-exo-trig cyclizations under metal-free neutral conditions.

Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones

Co-reporter:Dr. Bing Han;Xiu-Long Yang;Dr. Ran Fang;Dr. Wei Yu;Chao Wang;Xiao-Yong Duan ;Shuai Liu

Angewandte Chemie 2012 Volume 124( Issue 35) pp:8946-8950

Publication Date(Web):

DOI:10.1002/ange.201203799

CuCl/DABCO/4-HO-TEMPO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted Quinazolines and 4H-3,1-Benzoxazines

Co-reporter:Bing Han, Xiu-Long Yang, Chao Wang, Yong-Wei Bai, Tai-Chao Pan, Xin Chen, and Wei Yu

The Journal of Organic Chemistry 2012 Volume 77(Issue 2) pp:1136-1142

Publication Date(Web):December 14, 2011

DOI:10.1021/jo2020399

The Cu/N-ligand/TEMPO catalytic system was first applied to the aerobic oxidative synthesis of heterocycles. As demonstrated, 2-substituted quinazolines and 4H-3,1-benzoxazines were synthesized efficiently from the one-pot reaction of aldehydes with 2-aminobenzylamines and 2-aminobenzyl alcohols, respectively, by employing CuCl/DABCO/4-HO-TEMPO as the catalysts and oxygen as the terminal oxidant.

Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones

Co-reporter:Dr. Bing Han;Xiu-Long Yang;Dr. Ran Fang;Dr. Wei Yu;Chao Wang;Xiao-Yong Duan ;Shuai Liu

Angewandte Chemie International Edition 2012 Volume 51( Issue 35) pp:8816-8820

Publication Date(Web):

DOI:10.1002/anie.201203799

TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones—synthesis of imidazo[1,2-a]pyridines

Co-reporter:Lijuan Ma, Xianpei Wang, Wei Yu and Bing Han

Chemical Communications 2011 vol. 47(Issue 40) pp:11333-11335

Publication Date(Web):30 Aug 2011

DOI:10.1039/C1CC13568F

TBAI could catalyze the direct oxidative C–N coupling of 2-aminopyridines with β-keto esters and 1,3-diones, which affords imidazo[1,2-a]pyridines as the products. The reaction was realized under metal-free conditions by using tert-butyl hydroperoxide (TBHP) as the oxidant.

Efficient aerobic oxidative synthesis of 2-aryl quinazolinesviabenzyl C–H bond amination catalyzed by 4-hydroxy-TEMPO

Co-reporter:Bing Han, Chao Wang, Run-Feng Han, Wei Yu, Xiao-Yong Duan, Ran Fang and Xiu-Long Yang

Chemical Communications 2011 vol. 47(Issue 27) pp:7818-7820

Publication Date(Web):09 Jun 2011

DOI:10.1039/C1CC12308D

A novel and efficient aerobic protocol for the oxidative synthesis of 2-aryl quinazolinesviabenzyl C-H bond amination by a one-pot reaction of arylmethanamines with 2-aminobenzoketones and 2-aminobenzaldehydes has been carried out using the 4-hydroxy-TEMPO radical as the catalyst, without any metals or additives.

Efficient aerobic oxidative dehydrogenation of dihydropyrimidinones and dihydropyrimidines

Co-reporter:Bing Han, Run-Feng Han, Yu-Wei Ren, Xiao-Yong Duan, Yi-Chuan Xu, Wei Zhang

Tetrahedron 2011 67(31) pp: 5615-5620

Publication Date(Web):

DOI:10.1016/j.tet.2011.05.105

Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO

Co-reporter:Yong-Xing Chen;Ling-Feng Qian;Wei Zhang Dr. Dr.

Angewandte Chemie International Edition 2008 Volume 47( Issue 48) pp:9330-9333

Publication Date(Web):

DOI:10.1002/anie.200803381

Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO

Co-reporter:Yong-Xing Chen;Ling-Feng Qian;Wei Zhang Dr. Dr.

Angewandte Chemie 2008 Volume 120( Issue 48) pp:9470-9473

Publication Date(Web):

DOI:10.1002/ange.200803381

TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones—synthesis of imidazo[1,2-a]pyridines

Co-reporter:Lijuan Ma, Xianpei Wang, Wei Yu and Bing Han

Chemical Communications 2011 - vol. 47(Issue 40) pp:NaN11335-11335

Publication Date(Web):2011/08/30

DOI:10.1039/C1CC13568F

Efficient aerobic oxidative synthesis of 2-aryl quinazolinesviabenzyl C–H bond amination catalyzed by 4-hydroxy-TEMPO

Co-reporter:Bing Han, Chao Wang, Run-Feng Han, Wei Yu, Xiao-Yong Duan, Ran Fang and Xiu-Long Yang

Chemical Communications 2011 - vol. 47(Issue 27) pp:NaN7820-7820

Publication Date(Web):2011/06/09

DOI:10.1039/C1CC12308D

tert-Butyl nitrite-mediated vicinal sulfoximation of alkenes with sulfinic acids: a highly efficient approach toward α-sulfonyl ketoximes

Co-reporter:Fei Chen, Neng-Neng Zhou, Jun-Long Zhan, Bing Han and Wei Yu

Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 1) pp:NaN139-139

Publication Date(Web):2016/10/26

DOI:10.1039/C6QO00535G

Synthesis of isoxazoline-featured oxindoles by iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkenes

Co-reporter:Xiu-Long Yang, Yan Long, Fei Chen and Bing Han

Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 2) pp:NaN189-189

Publication Date(Web):2015/12/11

DOI:10.1039/C5QO00352K

A novel, selective and metal-free iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of unactivated alkenes and activated alkenes via tandem O–C/C–C/C–C bond formation was developed. By using this protocol, isoxazoline-featured oxindoles were successfully synthesized by a one-pot reaction using β,γ-unsaturated ketoximes and N-arylacrylamides as readily accessible substrates and TBHP as the commercially available oxidant.