Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

被引:91
|
作者
Liu, Zhen [1 ]
Derosa, Joseph [1 ]
Engle, Keary M. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
关键词
PALLADIUM-CATALYZED HYDROARYLATION; RH/M-TPPTC CATALYST; ARYLBORONIC ACIDS; ORGANOBORONIC ACIDS; BORONIC ACIDS; TRISUBSTITUTED ALKENES; RHODIUM; CYCLIZATION; YNAMIDES; SYSTEM;
D O I
10.1021/jacs.6b08818
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein-selectivity is controlled by a cleavable bidentate directing group: Under the optimized reaction conditions, both dialkyl and alkylaryl substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.
引用
收藏
页码:13076 / 13081
页数:6
相关论文
共 50 条
  • [41] Highly regioselective hydroselenation and double-bond isomerization of terminal alkynes with benzeneselenol catalyzed by bis(triphenylphosphine)palladium(II) dichloride
    Ozaki, Toshiya
    Kotani, Mao
    Kusano, Hiroki
    Nomoto, Akihiro
    Ogawa, Akiya
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 450 - 455
  • [42] Geometry-Constrained Iminopyridyl Palladium-Catalyzed Hydroarylation of Alkynes to Prepare Tri-substituted Alkenes Using Alcohol as Reductant
    Wu, Ke
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    Jin, Liqun
    Hu, Xinquan
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) : 3038 - 3043
  • [43] Interplay of terminal amino group and coordinating side chains in directing regioselective cleavage of natural peptides and proteins with palladium(II) complexes
    Milovic, NM
    Kostic, NM
    INORGANIC CHEMISTRY, 2002, 41 (26) : 7053 - 7063
  • [44] Palladium-Catalyzed C-H Arylation Using Phosphoramidate as a Directing Group at Room Temperature
    Chary, Bathoju Chandra
    Kim, Sunggak
    Park, Youngchul
    Kim, Jinsik
    Lee, Phil Ho
    ORGANIC LETTERS, 2013, 15 (11) : 2692 - 2695
  • [45] Palladium catalyzed acetoxylation of benzylic C-H bonds using a bidentate picolinamide directing group
    Cheng, Tao
    Yin, Weiyu
    Zhang, Yi
    Zhang, Yingnan
    Huang, Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (09) : 1405 - 1411
  • [46] Palladium-Catalyzed Late-Stage ortho-C-H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group
    Chu, Jean-Ho
    Chiang, Meng-Fan
    Li, Chin-Wei
    Su, Zhe-Hong
    Lo, Shao-Chi
    Wu, Ming-Jung
    ORGANOMETALLICS, 2019, 38 (09) : 2105 - 2119
  • [47] Pd(II)-Catalyzed Transient Directing Group-Assisted Regioselective Diverse C4-H Functionalizations of Indoles
    Singh, Anurag
    Dey, Arnab
    Pal, Kuntal
    Dash, Om Prakash
    Volla, Chandra M. R.
    ORGANIC LETTERS, 2022, 24 (10) : 1941 - 1946
  • [48] Palladium(II)-catalyzed ortho-C-H olefination of phenylalanine and phenylethylamine derivatives directed by removable picolinamide group
    Zhao, Fei
    Jia, Xiuwen
    Zhao, Jingwei
    Fei, Chaoli
    Liu, Liyang
    Liu, Guannan
    Wang, Dongping
    Chen, Fei
    RSC ADVANCES, 2017, 7 (40) : 25031 - 25040
  • [49] Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines
    Tsukamoto, Hirokazu
    Ikeda, Taishi
    Doi, Takayuki
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05): : 1733 - 1745
  • [50] Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp3)H Activation by Palladium Catalysis (vol 54, pg 13686, 2015)
    Zhang, Y. -F.
    Zhao, H. -W.
    Wang, H.
    Wei, J. -B.
    Shi, Z. -J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13492 - 13492