Bin Li

Find an error

Name: 李滨; Bin Li

Organization: Nankai University , China

Department: College of Chemistry

Title: Associate Professor(PhD)

TOPICS

Organic Chemistry

C-H Activation

Polymer

Stimuli Responsive Polymers Stimuli Responsive Polymers Temperature Responsive Polymers

Chemicals
References

Synthesis of 3-Arylbenzofuran-2-ylphosphines via Rhodium-Catalyzed Redox-Neutral C–H Activation and Their Applications in Palladium-Catalyzed Cross-Coupling of Aryl Chlorides

Co-reporter:Huanan Wang, Baiquan Wang, and Bin Li

The Journal of Organic Chemistry September 15, 2017 Volume 82(Issue 18) pp:9560-9560

Publication Date(Web):August 21, 2017

DOI:10.1021/acs.joc.7b01566

A new class of aryl-heteroarylphosphines, 3-arylbenzofuran-2-ylphosphines, was synthesized by [Cp*Rh(III)]-catalyzed redox-neutral cyclization of N-phenoxyacetamides with 1-alkynylphosphine sulfides and oxides followed by reduction. This step-economic reaction proceeds in excellent regioselectivity with a broad substrate scope. The application of the resulting air-stable trivalent-phosphine containing dicyclohexylphosphino moiety in palladium-catalyzed Suzuki–Miyaura coupling and Buchwald–Hartwig amination of aryl chlorides is also described.

Rhodium-Catalyzed Annulation of Tertiary Aniline N-Oxides to N-Alkylindoles: Regioselective C–H Activation, Oxygen-Atom Transfer, and N-Dealkylative Cyclization

Co-reporter:Bin Li, Hong Xu, Huanan Wang, and Baiquan Wang

ACS Catalysis 2016 Volume 6(Issue 6) pp:3856

Publication Date(Web):May 6, 2016

DOI:10.1021/acscatal.6b00311

[Cp*RhIII]-catalyzed annulation of tertiary aniline N-oxides with alkynes was reported to achieve the challenging ortho C–H functionalization of tertiary anilines via N–O bond acting as a traceless directing group. More significantly, this system represents the first example which integrates C–H activation, oxygen-atom transfer, and N-dealkylative cyclization in one reaction. This unprecedented coupling reaction has allowed the construction of N-alkylindole derivatives in high efficiency with broad substrate scope and good functional group tolerance.Keywords: cyclization; C−H activation; C−N bond cleavage; oxygen-atom transfer; tertiary aniline N-oxides

Rhodium(III)-Catalyzed C–H Activation and Annulation with 1-Alkynylphosphine Sulfides: A Mild and Regioselective Access for the Synthesis of Bulky Phosphine Ligands

Co-reporter:Bin Li, Jie Yang, Hong Xu, Haibin Song, and Baiquan Wang

The Journal of Organic Chemistry 2015 Volume 80(Issue 24) pp:12397-12409

Publication Date(Web):November 23, 2015

DOI:10.1021/acs.joc.5b02265

We reported herein rhodium(III)-catalyzed C–H activation and annulation reactions for the synthesis of bulky phosphine ligands by using 1-alkynylphosphine sulfides as key starting materials. In the presence of [Cp*RhCl2]2 (5 mol %) and CsOAc (2.0 equiv), various N-(pivaloyloxy)benzamides (3.0 equiv) could react smoothly with 1-alkynylphosphine sulfides at 40 °C in MeOH/CF3CH2OH cosolvent without external oxidant. Using [CpPhRhCl2]2 as catalyst, the reaction can be performed under less loading of benzamides (2.0 equiv) and milder reaction conditions (25 °C) with higher regioselectivity. In a sequential cyclization/desulfidation process, this new method provides a variety of bulky heteroarylphosphines with an isoquinolin-1(2H)-one motif.

Regioselective Ortho Olefination of Aryl Sulfonamide via Rhodium-Catalyzed Direct C–H Bond Activation

Co-reporter:Weijia Xie, Jie Yang, Baiquan Wang, and Bin Li

The Journal of Organic Chemistry 2014 Volume 79(Issue 17) pp:8278-8287

Publication Date(Web):August 2, 2014

DOI:10.1021/jo5015239

Rh(III)-catalyzed ortho C–H olefination of aryl sulfonamide directed by the SO2NHAc group is reported. This oxidative coupling process is achieved highly efficiently and selectively with a broad substrate scope. The reactions of N-tosylacetamide with acrylate esters afford ortho-alkenylated benzofused five-membered cyclic sulfonamides, whereas styrenes provide the direct diolefination products.

Ruthenium-Catalyzed Pyrrole Synthesis via Oxidative Annulation of Enamides and Alkynes

Co-reporter:Bin Li, Nuancheng Wang, Yujie Liang, Shansheng Xu, and Baiquan Wang

Organic Letters 2013 Volume 15(Issue 1) pp:136-139

Publication Date(Web):December 12, 2012

DOI:10.1021/ol303159h

An efficient and regioselective ruthenium-catalyzed oxidative annulation of enamides with alkynes via the cleavage of C(sp2)–H/N–H bonds is reported. The reactions can afford N-acetyl substituted or N-unsubstituted pyrroles by altering the reaction conditions slightly.

Regio- and Stereoselective Olefination of Phenol Carbamates through CH Bond Functionalization

Co-reporter:Bin Li;Jianfeng Ma;Yujie Liang;Nuancheng Wang;Shansheng Xu;Haibin Song;Baiquan Wang

European Journal of Organic Chemistry 2013 Volume 2013( Issue 10) pp:1950-1962

Publication Date(Web):

DOI:10.1002/ejoc.201201574

Abstract

Two pathways that can be used to access ortho-olefinated phenol carbamate, including a ruthenium(II)-catalyzed oxidative olefination of phenol carbamate with acrylates and a rhodium(III)-catalyzed alkyne hydroarylation of phenol carbamate with internal alkynes through direct C–H activation, are reported. Both reactions afford substituted alkenes in a highly regio- and stereoselective manner.

Ruthenium-Catalyzed Regioselective C2 Alkenylation of Indoles and Pyrroles via C–H Bond Functionalization

Co-reporter:Bin Li, Jianfeng Ma, Weijia Xie, Haibin Song, Shansheng Xu, and Baiquan Wang

The Journal of Organic Chemistry 2013 Volume 78(Issue 18) pp:9345-9353

Publication Date(Web):August 28, 2013

DOI:10.1021/jo401579m

An efficient ruthenium-catalyzed oxidative coupling of indoles and pyrroles with various alkenes at the C2-position assisted by employing the N,N-dimethylcarbamoyl moiety as a directing group is reported. The catalytic reaction proceeds in an excellent regio- and stereoselective manner.

Regioselective C2 Oxidative Olefination of Indoles and Pyrroles through Cationic Rhodium(III)-Catalyzed CH Bond Activation

Co-reporter:Dr. Bin Li;Jianfeng Ma;Weijia Xie;Dr. Haibin Song; Shansheng Xu;Dr. Baiquan Wang

Chemistry - A European Journal 2013 Volume 19( Issue 36) pp:11863-11868

Publication Date(Web):

DOI:10.1002/chem.201301987

Investigation and Comparison of the Mechanistic Steps in the [(Cp*MCl2)2] (Cp*=C5Me5; M=Rh, Ir)-Catalyzed Oxidative Annulation of Isoquinolones with Alkynes

Co-reporter:Nuancheng Wang;Dr. Bin Li;Dr. Haibin Song; Shansheng Xu;Dr. Baiquan Wang

Chemistry - A European Journal 2013 Volume 19( Issue 1) pp:358-364

Publication Date(Web):

DOI:10.1002/chem.201203374

Abstract

The mechanism of the [(Cp*MCl₂)₂] (M=Rh, Ir)-catalyzed oxidative annulation reaction of isoquinolones with alkynes was investigated in detail. In the first acetate-assisted CH-activation process (cyclometalated step) and the subsequent mono-alkyne insertion into the MC bonds of the cyclometalated compounds, both Rh and Ir complexes participated well. However, the desired final products, dibenzo[a,g]quinolizin-8-one derivatives, were only formed in high yield when the Rh species participated in the final oxidative coupling of the CN bond. Moreover, a Rh^I sandwich intermediate was isolated during this transformation. The iridium complexes were found to be inactive in the oxidative coupling processes. All of the relevant intermediates were fully characterized and determined by single-crystal X-ray diffraction analysis. Based on this mechanistic study, a Rh^IIIRh^IRh^III catalytic cycle was proposed for this reaction.

Ruthenium-Catalyzed Oxidative C–H Bond Olefination of N-Methoxybenzamides Using an Oxidizing Directing Group

Co-reporter:Bin Li, Jianfeng Ma, Nuancheng Wang, Huiliang Feng, Shansheng Xu, and Baiquan Wang

Organic Letters 2012 Volume 14(Issue 3) pp:736-739

Publication Date(Web):January 18, 2012

DOI:10.1021/ol2032575

Ruthenium-catalyzed oxidative C–H bond olefination of N-methoxybenzamides using an oxidizing directing group with a broad substrate scope is reported. The reactions of N-methoxybenzamides with acrylates in MeOH and styrene (or norbornadiene) in CF3CH2OH afforded two types of products.

Ruthenium-Catalyzed Oxidative Coupling/Cyclization of Isoquinolones with Alkynes through CH/NH Activation: Mechanism Study and Synthesis of Dibenzo[a,g]quinolizin-8-one Derivatives

Co-reporter:Dr. Bin Li;Huiliang Feng;Nuancheng Wang;Jianfeng Ma;Dr. Haibin Song; Shansheng Xu;Dr. Baiquan Wang

Chemistry - A European Journal 2012 Volume 18( Issue 40) pp:12873-12879

Publication Date(Web):

DOI:10.1002/chem.201201862

Abstract

The mechanism of [{RuCl₂(p-cymene)}₂]-catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate-assisted CH bond activation process to form cyclometalated compounds. Subsequent mono-alkyne insertion of the RuC bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the CN bond of the insertion compounds occurs to afford Ru⁰ sandwich complexes that undergo oxidation to regenerate the catalytically active Ru^II complex with the copper oxidant and release the desired dibenzo[a,g]quinolizin-8-one derivatives. All of the relevant intermediates were fully characterized and determined by single crystal X-ray diffraction analysis. The [{RuCl₂(p-cymene)}₂]-catalyzed CH bond functionalization of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through CH/NH activation was also demonstrated.