近年来,有关N-杂环卡宾(NHC)的合成、催化性能及其应用得到了快速发展,特别是在催化选择性有机反应领域,NHC类催化剂显示出催化效率高、选择性好及性能优异等特点,而引起人们极大的关注.本文从区域选择性、顺反异构选择性及手性选择性等方面综述了NHC催化选择性有机反应的最新进展,并予以了展望.
参考文献
| [1] | Arduengo A J,Harlow R L,Kilne M.A Stable Crystalline Carbene[J].J Am Chem Soc,1991,113(1):361-363. |
| [2] | SUN Xiaoyu,WU Jie.N-Heterocyclic Carbene:A Versatile Organocatalyst[J].Chinese J Org Chem,2006,26(6):745-756(in Chinese).孙小宇,吴劼.N-杂环卡宾:一种多用途有机小分子催化剂[J].有机化学,2006,26(6):745-756. |
| [3] | Fortman G C,Nolan S P.N-Heterocyclic Carbene(NHC) Ligands and Palladium in Homogeneous Cross-Coupling Catalysis:A Perfect Union[J].Chem Soc Rev,2011,40(10):5151-5169. |
| [4] | Sun W Y,Chow A L F,Li X H,et al.Luminescent Cyclometalated Platinum (Ⅱ) Complexes Containing N-Heterocyclic Carbene Ligands with Potent in Vitro and in Vivo Anti-Cancer Properties Accumulate in Cytoplasmic Structures of Cancer Cells[J].Chem Sci,2011,2(4):728-736. |
| [5] | Liu W K,Bensdorf K,Hagenbach A,et al.Synthesis and Biological Studies of Silver N-Heterocyclic Carbene Complexes Derived from 4,5-Diarylimidazole[J].Eur J Med Chem,2011,46(12):5927-5934. |
| [6] | Rubbian R,Can S Z,Kitanovic I,et al.Comparative in Vitro Evaluation of N-Heterocyclic Carbene Gold(Ⅰ) Complexes of the Benzimidazolylidene Type[J].J Med Chem,2011,54(24):8646-8657. |
| [7] | Mercs L,Albrecht M.Beyond Catalysis:N-Heterocyclic Carbene Complexes as Components for Medicinal,Luminescent,and Functional Materials Applications[J].Chem Soc Rev,2010,39(6):1903-1912. |
| [8] | Ho C Y,He L.Catalytic Intermolecular Tail-to-Tail Hydroalkenylation of Styrenes with α-Olefins:Regioselective Migratory Insertion Controlled by a Nickel/N-Heterocyclic Carbene[J].Angew Chem Int Ed,2010,49(48):9182-9186. |
| [9] | Singh S,Rai V K,Singh P,et al.Expeditious Synthesis of Functionalized Piperidines by Regioselective Ring Opening of Aziridines by Enals Catalyzed by an N-Heterocyclic Carbene[J].Synthesis,2010,17:2957-2964. |
| [10] | Urban S,Ortega N,Glorius F.Ligand-Controlled Highly Regioselective and Asymmetric Hydrogenation of Quinoxalines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes[J].Angew Chem Int Ed,2011,50 (16):3803-3806. |
| [11] | Zhao Q W,Curran D P,Malacria M,et al.NHC-Catalyzed Chemo-and Regioselective Hydrosilylation of Carbonyl Derivatives[J].Synlett,2012,(1):433-437. |
| [12] | Cardinal-David B,Raup D E A,Scheidt A.Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates[J].J Am Chem Soc,2010,132(15):5345-5347. |
| [13] | Feng J J,Zhang J L.An Atom-Economic Synthesis of Bicyclo[3.1.0]Hexanes by Rhodium N-Heterocyclic CarbeneCatalyzed Diastereoselective Tandem Hetero-[5 + 2]Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes[J].J Am Chem Soc,2011,133(19):7304-7307. |
| [14] | Sun F G,Ye S.Diastereoselective Synthesis of 3-Hydroxyindanones via N-Heterocyclic Carbene Catalyzed[4 + 1]Annulation of Phthalaldehyde and 1,2-Diactivated Michael Acceptors[J].Synlett,2011,(3):1005-1009. |
| [15] | Kawanaka Y,Phillips E M,Scheidt K A.N-Heterocyclic Carbene-Catalyzed Enantioselective Mannich Reactions with α-Aryloxyacetaldehydes[J].J Am Chem Soc,2009,131(50):18028-18029. |
| [16] | Zhang Y R,He L,Wu X,et al.Chiral N-Heterocyclic Carbene Catalyzed Staudinger Reaction of Ketenes with Imines:Highly Enantioselective Synthesis of N-Boo β-Lactams[J].Org Lett,2008,10(2):277-280. |
| [17] | Wang X N,Lv H,Huang X L.Asymmetric Esterification of Ketenes Catalyzed by An N-Heterocyclic Carbene[J].Org Biomol Chem,2009,7:346-3 50. |
| [18] | Lv H,You L,Ye S.Enantioselective Synthesis of Dihydrocoumarins via N-Heterocyclic Carbene-Catalyzed Cycloaddition of Ketenes and o-Quinone Methides[J].Adv Synth Catal,2009,351(17):2822-2826. |
| [19] | Jian T Y,He L,Tang C,et al.N-Heterocyclic Carbene Catalysis:Enantioselective Formal[2 + 2]Cycloaddition of Ketenes and N-Sulfinylanilines[J].Angew Chem Int Ed,2011,50(39):9104-9107. |
| [20] | Cheng Y,Peng J H,Li Y J,et al.N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes:Controllable Stereoselective Synthesis of Polyhydroxylated Spiro-and Fused Indenonesdictated by the Structure of NHC Catalysts[J].J Org Chem,2011,76(6):1844-1851. |
| [21] | Enders D,Grossmann A,Fronert J,et al.N-Heterocyclic Carbene Catalysed Asymmetric Cross-Benzoin Reactions of Heteroaromatic Aldehydes with Trifluoromethyl Ketones[J].Chem Commun,2010,46(34):6282-6284. |
| [22] | Enders D,Han J,Henseler A.Asymmetric Intermolecular Stetter Reactions Catalyzed by a Novel Triazolium Derived N-Heterocyclic Carbene[J].Chem Commun,2008,44 (34):3989-3991. |
| [23] | Lathrop S P,Rovis T.Asymmetric Synthesis of Functionalized Cyclopentanones via a Multicatalytic Secondary Amine/N-Heterocyclic Carbene Catalyzed Cascade Sequence[J].J Am Chem Soc,2009,131(38):13628-13630. |
| [24] | Zhao X D,DiRocco D A,Rovis T.N-Heterocyclic Carbene and Br(o)nsted Acid Cooperative Catalysis:Asymmetric Synthesis of Trans-γ-Lactams[J].J Am Chem Soc,2011,133(32):12466-12469. |
| [25] | Zhu Z Q,Zheng X L,Jiang N F,et al.Chiral N-Heterocyclic Carbene Catalyzed Annulation of α,β-Unsaturated Aldehydes with 1,3-Dicarbonyls[J].Chem Commun,2011,47(30):8670-8672. |
| [26] | Biswas A,Sarkar S D,Tebben L,et al.Enantioselective Cyclopropanation of Enals by Oxidative N-Heterocyclic Carbene Catalysis[J].Chem Commun,2012,48(42):5190-5192. |
| [27] | Chaulagain M R,Sormunen G J,Montgomery J.New N-Heterocyclic Carbene Ligand and Its Application in Asymmetric Nickel-Catalyzed Aldehyde/Alkyne Reductive Couplings[J].J Am Chem Soc,2007,129 (31):9568-9569. |
| [28] | Selim K B,Nakanishi H,Matsumoto Y,et al.Chiral N-Heterocyclic Carbene-Copper (Ⅰ)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides:Steric and Electronic Effects on γ-Selectivity[J].J Org Chem,2011,76(5):1398-1408. |
| [29] | Lee K S,Hoveyda A H.Monodentate Non-C2-Symmetric Chiral N-Heterocyclic Carbene Complexes for Enantioselective Synthesis.Cu-Catalyzed Conjugate Additions of Aryl-and Alkenylsilylfluorides to Cyclic Enones[J].J Org Chem,2009,74(12):4455-4462. |
| [30] | Lindsay D M,McArthur D.The Synthesis of Chiral N-Heterocyclic Carbene-Borane and-Diorganoborane Complexes and Their Use in the Asymmetric Reduction of Ketones[J].Chem Commun,2010,46 (14):2474-2476. |
| [31] | Yang J M,Zhang R,Wang W F,et al.Axially Chiral N-Heterocyclic Carbene Gold(Ⅰ) Complex Catalyzed Asymmetric Friedel-Crafts/Cyclization Reaction of Nitrogen-tethered 1,6-Enynes with Indole Derivatives[J].Tetrahedron:Asymm,2011,22(23):2029-2038. |
| [32] | Ma G N,Zhang T,Shi M.Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C2-Symmetric Cationic N-Heterocyclic Carbene Pd2 + Diaquo Complexes[J].Org Lett,2009,11 (4):875-878. |
| [33] | Zhang R,Xu Q,Zhang X,et al.Axially Chiral C2-Symmetric N-Heterocyclic Carbene (NHC) Palladium ComplexesCatalyzed Asymmetric Arylation of Aldehydes with Arylboronic Acids[J].Tetrahedron:Asymm,2010,21 (15):1928-1935. |
| [34] | Xu L,Shi Y.Chiral N-Heterocyclic Carbene-Pd (0)-Catalyzed Asymmetric Diamination of Conjugated Dienes and Triene[J].J Org Chem,2008,73(2):749-751. |
| [35] | Liu L,Ishida N,Ashida S,et al.Synthesis of Chiral N-Heterocyclic Carbene Ligands with Rigid Backbones and Application to the Palladium-Catalyzed Enantioselective Intramolecular α-Arylation of Amides[J].Org Lett,2011,13:1666-1669. |
| [36] | DiRocco D A,Rovis T.Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode:N-Heterocyclic Carbene and Photoredox Catalysis[J].J Am Chem Soc,2012,134 (19):8094-8097. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%