Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation

被引：36
|
作者：
Shimogaki, Mio [1 ]
Fujita, Morifumi [1 ]
Sugimura, Takashi [1 ]
机构：
[1] Univ Hyogo, Grad Sch Mat Sci, 3-2-1 Kohto, Kamigori, Hyogo, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 51期
基金：
日本学术振兴会;
关键词：
cyclization; enantioselectivity; heterocycles; hypervalent compounds; oxidation; ASYMMETRIC-SYNTHESIS; REAGENTS; DIAMINATION; FUNCTIONALIZATION; DIFLUORINATION; REARRANGEMENTS; CATALYSTS; KETONES;
D O I：
10.1002/anie.201609110
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.
引用
收藏
页码：15797 / 15801
页数：5
相关论文
共 50 条
  • [31] A metal-free approach for the synthesis of amides/esters with pyridinium salts of phenacyl bromides via oxidative C-C bond cleavage
    Manasa, Kesari Lakshmi
    Tangella, Yellaiah
    Krishna, Namballa Hari
    Alvala, Mallika
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 1864 - 1871
  • [32] Metal-Free Tandem Oxidative Aryl Migration and C-C Bond Cleavage: Synthesis of α-Ketoamides and Esters from Acrylic Derivatives
    Liu, Le
    Du, Liang
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ORGANIC LETTERS, 2014, 16 (21) : 5772 - 5775
  • [33] Hypervalent iodine mediated oxidative radical amination of heteroarenes under metal-free conditions
    Zhao, Feng
    Sun, Ting
    Sun, Hefeng
    Xi, Gaolei
    Sun, Kai
    TETRAHEDRON LETTERS, 2017, 58 (32) : 3132 - 3135
  • [34] Metal-free synthesis of indolizines through oxidative C-C and C-N bond formations of C (sp3)-H bonds
    Reddy, N. Naresh Kumar
    Mohan, Darapaneni Chandra
    Adimurthy, Subbarayappa
    TETRAHEDRON LETTERS, 2016, 57 (10) : 1074 - 1078
  • [35] Metal-free C-C bond formation via coupling of nitrile imines and boronic acids
    Livingstone, Keith
    Bertrand, Sophie
    Mowat, Jenna
    Jamieson, Craig
    CHEMICAL SCIENCE, 2019, 10 (44) : 10412 - 10416
  • [36] A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes
    Qin, Qixue
    Wang, Weijing
    Zhang, Cheng
    Song, Song
    Jiao, Ning
    CHEMICAL COMMUNICATIONS, 2019, 55 (71) : 10583 - 10586
  • [37] Metal-free desilylative C-C bond formation by visible-light photoredox catalysis
    Uygur, Mustafa
    Danelzik, Tobias
    Mancheno, Olga Garcia
    CHEMICAL COMMUNICATIONS, 2019, 55 (20) : 2980 - 2983
  • [38] Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
    Yu, Pei
    Wang, Yuwei
    Zeng, Zhigang
    Chen, Yunfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22): : 14883 - 14891
  • [39] Metal-Free Oxidative C-H Bond Amination at Ambient Temperature
    Samanta, Rajarshi
    Antonchick, Andrey P.
    SYNLETT, 2012, (06) : 809 - 813
  • [40] Metal-free nitro-carbocyclization of activated alkenes: a direct approach to synthesize oxindoles by cascade C-N and C-C bond formation
    Shen, Tao
    Yuan, Yizhi
    Jiao, Ning
    CHEMICAL COMMUNICATIONS, 2014, 50 (05) : 554 - 556
12345