Cobalt-catalyzed regioselective hydroazidation of 1-aryl-1,3-dienes: facile access to allylic azides

被引:2
|
作者
Shen, Mei-Hua [1 ]
Qi, Xiao-Wen [1 ]
Li, De-Xia [1 ]
Wang, Xin-Yi [1 ]
Zhu, Chi-Fan [1 ]
Xu, Hua-Dong [1 ]
机构
[1] Changzhou Univ, Sch Pharm, Changzhou 213164, Jiangsu, Peoples R China
关键词
UNACTIVATED OLEFINS; CLICK CHEMISTRY; ORGANIC AZIDES; CARBON BONDS; HYDROHYDRAZINATION; COMPLEXES; HYDROFUNCTIONALIZATION; HYDROALKOXYLATION; HYDROAMINATION; DIVERSITY;
D O I
10.1039/d3qo00431g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new cobalt-catalyzed hydroazidation of 1-aryl-1,3-dienes by using TMSN3 as a nucleophilic azide source under mild conditions has been reported, leading to the synthesis of a wide range of allylic azides with moderate to good yields. This oxidative MHAT hydroazidation achieved excellent regioselectivity towards 1,2-addition products through an S(N)2-like pathway between in situ generated allyl cobalt(iv) species and TMSN3.
引用
收藏
页码:3010 / 3015
页数:6
相关论文
共 50 条
  • [1] Cobalt-Catalyzed 1,4-Hydrobutadienylation of 1-Aryl-1,3-dienes with 2,3-Dimethyl-1,3-butadiene
    Bohn, Martin A.
    Schmidt, Anastasia
    Hilt, Gerhard
    Dindaroglu, Mehmet
    Schmalz, Hans-Guenther
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) : 9689 - 9693
  • [2] Cobalt-catalyzed hydroazidation of olefins: Convenient access to alkyl azides
    Waser, J
    Nambu, H
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8294 - 8295
  • [3] Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes
    Werth, Jacob
    Uyeda, Christopher
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13902 - 13906
  • [4] Cobalt-catalyzed asymmetric hydroboration of prochiral 1,3-dienes
    Duvvuri, Krishnaja
    Dewese, Kendra
    RajanBabu, T. V.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [5] Experimental and Theoretical Studies on Cobalt-Catalyzed Regioselective Hydrosilylation of Tetrafluorinated Cyclohexa-1,3-dienes
    Nagai, Kento
    Morishitabara, Suguru
    Nishi, Yuji
    Kajimoto, Chihiro
    Yasui, Motohiro
    Yumura, Takashi
    Yamada, Shigeyuki
    Konno, Tsutomu
    [J]. ORGANIC LETTERS, 2023, 25 (38) : 6975 - 6981
  • [6] Regioselective Hydroacylation of 1,3-Dienes by Cobalt Catalysis
    Chen, Qing-An
    Kim, Daniel K.
    Dong, Vy M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) : 3772 - 3775
  • [7] Cobalt-Catalyzed 1,4-Hydrovinylation of Styrenes and 1-Aryl-1,3-butadienes
    Hilt, Gerhard
    Danz, Michael
    Treutwein, Jonas
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3322 - 3325
  • [8] Cobalt-catalyzed hydrohydrazination of dienes and enynes:: Access to allylic and propargylic hydrazides
    Waser, J
    González-Gómez, JC
    Nambu, H
    Huber, P
    Carreíra, EM
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4249 - 4252
  • [9] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES
    AKERMARK, B
    NYSTROM, JE
    REIN, T
    BACKVALL, JE
    HELQUIST, P
    ASLANIAN, R
    [J]. TETRAHEDRON LETTERS, 1984, 25 (50) : 5719 - 5722
  • [10] TBAI-Catalyzed Regioselective Hydroxyperoxidation of 1-Aryl/Alkyl-1,3-dienes
    Kumar, Atul
    Khatun, Gulenur N.
    Fernandes, Rodney A.
    [J]. ORGANIC LETTERS, 2023, 25 (23) : 4313 - 4317