Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols

被引：59
|
作者：
Kang, Taeho [1 ]
Kim, Nana [1 ]
Cheng, Peter T. [2 ]
Zhang, Hao [2 ]
Foo, Klement [2 ]
Engle, Keary M. [1 ]
机构：
[1] Scripps Res, Dept Chem, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb Res & Early Dev, Discovery Chem, Princeton, NJ 08543 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 34期
基金：
美国国家科学基金会;
关键词：
3-COMPONENT CARBOAMINATION; ELECTROPHILIC AMINATION; SYN-CARBOAMINATION; HYDROAMINATION; CARBOALKOXYLATION; CONSTRUCTION; DERIVATIVES; ACCESS; ARYL;
D O I：
10.1021/jacs.1c07112
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyOhydroxylamine electrophiles that suppress competitive processes, including undesired beta-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with generally high regio- and syn-diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed svn-insertion of an organonickel(I) species.
引用
收藏
页码：13962 / 13970
页数：9
相关论文
共 50 条
  • [1] Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds
    van der Puyl, Vincent A.
    Derosa, Joseph
    Engle, Keary M.
    [J]. ACS CATALYSIS, 2019, 9 (01): : 224 - 229
  • [2] Nickel-Catalyzed Dearomative trans-1,2-Carboamination
    Hernandez, Lucas W.
    Klockner, Ulrich
    Pospech, Jola
    Hauss, Lilian
    Sarlah, David
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (13) : 4503 - 4507
  • [3] Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes
    He, Jun
    Xue, Yuhang
    Han, Bo
    Zhang, Chunzhu
    Wang, You
    Zhu, Shaolin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (06) : 2328 - 2332
  • [4] Alkene Difunctionalization Directed by Free Amines: DiamineSynthesis via Nickel-Catalyzed 1,2-Carboamination
    Kang, Taeho
    Gonzalez, Jose Manuel
    Li, Zi-Qi
    Foo, Klement
    Cheng, Peter T. W.
    Engle, Keary M.
    [J]. ACS CATALYSIS, 2022, 12 (07) : 3890 - 3896
  • [5] Nickel-Catalyzed Isomerization/Allylic Cyanation of Alkenyl Alcohols
    Ding, Ying
    Long, Jinguo
    Sun, Feilong
    Fang, Xianjie
    [J]. ORGANIC LETTERS, 2021, 23 (15) : 6073 - 6078
  • [6] Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides
    Derosa, Joseph
    Kleinmans, Roman
    Tran, Van T.
    Karunananda, Malkanthi K.
    Wisniewski, Steven R.
    Eastgate, Martin D.
    Engle, Keary M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (51) : 17878 - 17883
  • [7] Copper-Catalyzed Dearomative trans-1,2-Carboamination
    Davis, Christopher W.
    Li, Yanrong
    Zhang, Yu
    Siddiqi, Zohaib
    Liu, Peng
    Sarlah, David
    [J]. ACS CATALYSIS, 2024, 14 (13): : 10132 - 10137
  • [8] Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
    Derosa, Joseph
    van der Puyl, Vincent A.
    Tran, Van T.
    Liu, Mingyu
    Engle, Keary M.
    [J]. CHEMICAL SCIENCE, 2018, 9 (23) : 5278 - 5283
  • [9] Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds
    Li, Zi-Qi
    He, Wen-Ji
    Ni, Hui-Qi
    Engle, Keary M.
    [J]. CHEMICAL SCIENCE, 2022, 13 (22) : 6567 - 6572
  • [10] Distinct reactivity of Pd(OTs)2:: The intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes
    Houlden, Chris E.
    Bailey, Chris D.
    Ford, J. Gair
    Gagne, Michel R.
    Lloyd-Jones, Guy C.
    Booker-Milburn, Kevin I.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) : 10066 - +
12345