Photoredox Ni-Catalyzed Branch-Selective Reductive Coupling of Aldehydes with 1,3-Dienes

被引：66
作者：
Li, Yan-Lin [1 ,2 ]
Li, Wen-Duo [1 ,2 ]
Gu, Zheng-Yang [1 ]
Chen, Jie [1 ]
Xia, Ji-Bao [1 ]
机构：
[1] Lanzhou Inst Chem Phys LICP, Lanzhou, Gansu, Peoples R China
[2] Univ Chinese Acad Sci, Beijing, Peoples R China
来源：
ACS CATALYSIS | 2020年 / 10卷 / 02期
关键词：
synergistic catalysis; photoredox catalysis; nickel; reductive coupling; 1,3-diene; SINGLE-ELECTRON TRANSMETALATION; TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; NICKEL CATALYSIS; VISIBLE-LIGHT; DUAL CATALYSIS; ALLYLATION; DIENES; HOMOALLYLATION; ALCOHOL;
D O I：
10.1021/acscatal.9b05137
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
We report here a Ni-catalyzed reductive coupling of aldehydes with widely available 1,3-dienes under visible-light photoredox dual catalysis. The homoallyic alcohols are obtained in broad scope with complete branched regioselectivity. Hantzsch ester is used as the hydrogen radical source to oxidize low-valent nickel salt affording Ni-H species. Preliminary mechanistic studies indicate a successive single-electron transfer (SET) pathway and the generation of a key pi-allylnickel intermediate via Ni-H insertion of 1,3-diene in this synergistic catalytic process.
引用
收藏
页码：1528 / 1534
页数：13
相关论文
共 82 条
  • [71] Methods and Mechanisms for Cross-Electrophile Coupling of Csp2 Halides with Alkyl Electrophiles
    Weix, Daniel J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (06) : 1767 - 1775
  • [72] Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer
    Xiang, Ming
    Luo, Guoshun
    Wang, Yuankai
    Krische, Michael J.
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (07) : 981 - 984
  • [73] Enantioselective 1,2-Difunctionalization of 1,3-Butadiene by Sequential Alkylation and Carbonyl Allylation
    Xiong, Yang
    Zhang, Guozhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) : 2735 - 2738
  • [74] Visible-Light Photoredox Catalysis
    Xuan, Jun
    Xiao, Wen-Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) : 6828 - 6838
  • [75] Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols
    Yang, Yun
    Zhu, Shou-Fei
    Duan, Hai-Feng
    Zhou, Chang-Yue
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) : 2248 - +
  • [76] Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products
    Yus, Miguel
    Gonzalez-Gomez, Jose C.
    Foubelo, Francisco
    [J]. CHEMICAL REVIEWS, 2013, 113 (07) : 5595 - 5698
  • [77] Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines
    Yus, Miguel
    Gonzalez-Gomez, Jose C.
    Foubelo, Francisco
    [J]. CHEMICAL REVIEWS, 2011, 111 (12) : 7774 - 7854
  • [78] Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene
    Zbieg, Jason R.
    Yamaguchi, Eiji
    McInturff, Emma L.
    Krische, Michael J.
    [J]. SCIENCE, 2012, 336 (6079) : 324 - 327
  • [79] Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonyl syn-Crotylation from the Alcohol Oxidation Level
    Zbieg, Jason R.
    Moran, Joseph
    Krische, Michael J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) : 10582 - 10586
  • [80] Iridium-Catalyzed Hydrohydroxyalkylation of Butadiene: Carbonyl Crotylation
    Zbieg, Jason R.
    Fukuzumi, Takeo
    Krische, Michael J.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2416 - 2420
123456789