Rhodium(II)-Catalyzed N-H Insertions of Carbenes under Mechanochemical Conditions

被引:5
|
作者
Biswas, Sourav [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
DIAZOACETATES; BONDS; CATALYST; TOOL;
D O I
10.1021/acs.orglett.4c00216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under mechanochemical conditions in a mixer mill, Rh-2(OAc)(4) catalyzes the reaction between aryldiazoesters and anilines to give alpha-amino esters. The process proceeds under mild conditions and is insensitive to air. It is solvent-free and scalable. A broad substrate scope, short reaction times, operational simplicity, and good functional group tolerance are additional salient features of this protocol.
引用
收藏
页码:1511 / 1516
页数:6
相关论文
共 50 条
  • [1] Metal-Free N-H Insertions of Donor/Acceptor Carbenes
    Hansen, Stephanie R.
    Spangler, Jillian E.
    Hansen, Jorn H.
    Davies, Huw M. L.
    ORGANIC LETTERS, 2012, 14 (17) : 4626 - 4629
  • [2] Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions
    Muthusamy, Sengodagounder
    Karikalan, Thangaraju
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) : 9243 - 9256
  • [3] General Ir-Catalyzed N-H Insertions of Diazomalonates into Aliphatic and Aromatic Amines
    Zhong, Zhuang
    Besnard, Celine
    Lacour, Jerome
    ORGANIC LETTERS, 2024, 26 (05) : 983 - 987
  • [4] Asymmetric N-H Insertion Reaction Cooperatively Catalyzed by Rhodium and Chiral Spiro Phosphoric Acids
    Xu, Bin
    Zhu, Shou-Fei
    Xie, Xiu-Lan
    Shen, Jun-Jie
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11483 - 11486
  • [5] Rhodium(III)-Catalyzed N-H Insertion Reaction of Phosphoryl Amides withα-ArylDiazoesters for the Synthesis ofα-PhosphorylAmino Esters
    Son, Jeong-Yu
    Baek, Yonghyeon
    Kim, Sanghyuck
    Lee, Kyungsup
    Lee, Phil Ho
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2020, 41 (06) : 615 - 627
  • [6] Synthesis of Indoxylic Acid Esters by Rhodium-catalyzed Carbene N-H Insertion and Thermal Cyclization
    Honey, Mark A.
    Moody, Christopher J.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2014, 67 (8-9) : 1211 - 1216
  • [7] Ru(II)-Pheox catalyzed N-H insertion reaction of diazoacetamides: synthesis of N-substituted α-aminoamides
    Chanthamath, Soda
    Thongjareun, Songkharm
    Shibatomi, Kazutaka
    Iwasa, Seiji
    TETRAHEDRON LETTERS, 2012, 53 (36) : 4862 - 4865
  • [8] Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Organosilanes by Donor/Acceptor Carbenes Derived from Aryldiazoacetates
    Garlets, Zachary J.
    Hicks, Elliot F.
    Fu, Jiantao
    Voight, Eric A.
    Davies, Huw M. L.
    ORGANIC LETTERS, 2019, 21 (12) : 4910 - 4914
  • [9] Substitution pattern in ruthenium octa-n-butoxyphthalocyanine complexes influence their reactivity in N-H carbene insertions
    Kroitor, Andrey P.
    Dmitrienko, Alexander A.
    Martynov, Alexander G.
    Gorbunova, Yulia G.
    Sorokin, Alexander B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 21 (01) : 69 - 74
  • [10] Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds
    Burtoloso, Antonio C. B.
    Santiago, Joao V.
    Bernardim, Barbara
    Talero, Alexander G.
    CURRENT ORGANIC SYNTHESIS, 2015, 12 (05) : 650 - 659