Mild and Regioselective Benzylic C-H Functionalization: Ni-Catalyzed Reductive Arylation of Remote and Proximal Olefins

被引:257
|
作者
He, Yuli [1 ]
Cai, Yalei [1 ]
Zhu, Shaolin [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
关键词
ALKENE ISOMERIZATION; ALKYL BROMIDES; HYDROARYLATION; CO2; CARBOXYLATION; TOLTERODINE; ACTIVATION; COMPLEXES; SILANES; CUH;
D O I
10.1021/jacs.6b11962
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synergistic combination of NiH-catalyzed alkene isomerization with nickel-catalyzed cross-coupling has yielded a general protocol for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities from readily accessible olefin starting materials. Furthermore, the practicality and synthetic flexibility of this approach is highlighted by the successful employment of isomeric mixtures of olefins for regioconvergent arylation.
引用
收藏
页码:1061 / 1064
页数:4
相关论文
共 50 条
  • [1] Mild and Regioselective Benzylic C-H Functionalization: Ni-Catalyzed Reductive Arylation of Remote and Proximal Olefins (vol 139, pg 1061, 2017)
    He, Yuli
    Cai, Yalei
    Zhu, Shaolin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (05) : 2120 - 2120
  • [2] Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds
    Liu, Zhi-Yunc
    Cook, Silas P.
    [J]. ORGANIC LETTERS, 2022, 24 (18) : 3313 - 3318
  • [3] Diverting Ni-Catalyzed Direct Benzylic C-H Hydroxylation towards Trifluoroethoxylation
    Bushmin, Dmitry S.
    Samsonenko, Denis G.
    Talsi, Evgenii P.
    Lyakin, Oleg Y.
    Bryliakov, Konstantin P.
    [J]. CHEMCATCHEM, 2024, 16 (07)
  • [4] Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines
    Kim, Byeong-Seon
    Jimenez, Jacqueline
    Gao, Feng
    Wash, Patrick J.
    [J]. ORGANIC LETTERS, 2015, 17 (23) : 5788 - 5791
  • [5] Ni-Catalyzed Chelation-Assisted Direct Functionalization of Inert C-H Bonds
    Liu, Yan-Hua
    Xia, Yu-Nong
    Shi, Bing-Feng
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (06) : 635 - 662
  • [6] Tackling Remote sp3 C-H Functionalization via Ni-Catalyzed "chain-walking" Reactions
    Janssen-Mueller, Daniel
    Sahoo, Basudev
    Sun, Shang-Zheng
    Martin, Ruben
    [J]. ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) : 195 - 206
  • [7] Ni-catalyzed oxidative decarboxylative arylation of unactivated C-H bonds with (hetero)aryl benzoates
    Honeycutt, Aaron
    Hoover, Jessica
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [8] Pd-Catalyzed Arylation/Oxidation of Benzylic C-H Bond
    Xie, Yongju
    Yang, Yuzhu
    Huang, Lehao
    Zhang, Xunbin
    Zhang, Yuhong
    [J]. ORGANIC LETTERS, 2012, 14 (05) : 1238 - 1241
  • [9] Ni-Catalyzed C-H Arylation of Oxazoles and Benzoxazoles Using Pharmaceutically Relevant Aryl Chlorides and Bromides
    Larson, Helen
    Schultz, Danielle
    Kalyani, Dipannita
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13092 - 13103
  • [10] Ni-catalyzed undirected and regioselective acceptorless dehydrogenative silylation of primary benzylic C(sp3)-H bonds
    Yu, Qing
    Yatabe, Takafumi
    Matsuyama, Takehiro
    Yabe, Tomohiro
    Yamaguchi, Kazuya
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (10)