Catalyst-Controlled 1,2-and 1,1-Arylboration of -Alkyl Alkenyl Arenes

被引：79
|
作者：
Bergmann, Allison M. [1 ]
Dorn, Stanna K. [1 ]
Smith, Kevin B. [1 ]
Logan, Kaitlyn M. [1 ]
Brown, M. Kevin [1 ]
机构：
[1] Indiana Univ, Dept Chem, 800 E Kirkwood Ave, Bloomington, IN 47405 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 06期
关键词：
carboboration; copper; cross-coupling; homogeneous catalysis; palladium; CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE ARYLBORATION; REGIOSELECTIVE ARYLBORATION; ARYL BROMIDES; TERTIARY; COPPER; COMPLEXES; REAGENTS; 1,1-DIARYLATION; SECONDARY;
D O I：
10.1002/anie.201812533
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two methods are reported for the 1,2- and 1,1-arylboration of -methyl vinyl arenes. In the case of 1,2-arylboration, the formation of a quaternary center occurred through a rare cross-coupling reaction of a tertiary organometallic complex. 1,1-Arylboration was enabled by catalyst optimization and occurred through a -hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.
引用
收藏
页码：1719 / 1723
页数：5
相关论文
共 50 条
  • [21] Catalytic System-Controlled Regioselective 1,2-and 1,4-Carboannulations of [60]Fullerene
    Liu, Tong-Xin
    Ru, Yifei
    Guo, Wenyue
    Ma, Nana
    Yang, Panting
    Li, Xiaojun
    Zhang, Pengling
    Bi, Jingjing
    Zhang, Guisheng
    ORGANIC LETTERS, 2024, 26 (13) : 2552 - 2557
  • [22] Unimolecular rate constants for the 1,2-and 1,1-HF elimination from chemically activated 1,1,1,2,2-pentafluoroethane.
    Schiebel, HN
    Everett, WC
    Heard, GL
    Holmes, BE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U749 - U749
  • [23] Synthesis of Bulky 1,1-Diarylalkanes by Copper-Catalyzed 1,2-Alkylarylation of Styrenes with α-Carbonyl Alkyl Bromides and Arenes involving C-H Functionalization
    Luo, Shu-Zheng
    Min, Man-Yi
    Wu, Yan-Chen
    Jiang, Shuai-Shuai
    Xiao, Yu-Ting
    Song, Ren-Jie
    Li, Jin-Heng
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2921 - 2929
  • [24] Tests on alkali-organic compounds XV Controlled 1,2-and 1,4-Polymerisation of butadiene
    Ziegler, K
    Grimm, H
    Willer, R
    JUSTUS LIEBIGS ANNALEN DER CHEMIE, 1939, 542 : 90 - 122
  • [25] H-1-NMR-SPECTRA OF 1,1-ALKYL-PHENYL-HYDRAZINES AND 1,2-ALKYL-PHENYL-HYDRAZINES IN DIMETHYLSULFOXIDE - METHOD OF DIFFERENTIATION
    SCHANTL, J
    MULLER, EP
    MONATSHEFTE FUR CHEMIE, 1978, 109 (06): : 1481 - 1484
  • [26] Catalyst-Controlled Regiodivergent Synthesis of 1-and 3-Thiosugars with High Stereoselectivity and Chemoselectivity
    Liu, Yuexin
    Jiao, Yang
    Luo, Huajun
    Huang, Nianyu
    Lai, Mengnan
    Zou, Kun
    Yao, Hui
    ACS CATALYSIS, 2021, 11 (09): : 5287 - 5293
  • [27] Regioselective synthesis of 1,2-and 1,3-diaminothiacalix[4]arenes via nucleophilic aromatic substitution and their X-ray structures
    Katagiri, Hiroshi
    Tanaka, Shinya
    Ohkubo, Kazuya
    Akahira, Yuki
    Morohashi, Naoya
    Iki, Nobukiho
    Hattori, Tetsutaro
    Miyano, Sotaro
    RSC ADVANCES, 2014, 4 (19) : 9608 - 9616
  • [28] 1,1′-(Ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) as a recyclable catalyst for acylation
    Naik, Sarala
    Kavala, Veerababurao
    Gopinath, Rangam
    Patel, Bhisma K.
    ARKIVOC, 2006, : 21 - 36
  • [29] Electrochemical Oxidative Arylsulfonylation and 1,2-Alkyl Shift Sequences of Alkenyl Cyclobutanols for the Synthesis of β-Sulfonated Cyclopentanones
    Kim, Yebin
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (03) : 510 - 513
  • [30] DIRECT SYNTHESIS OF ALKYL CHLOROSILANES AND ALKENYL CHLOROSILANES ON THE BASIS OF 1,1-DICHLORETHANE AND 2,2-DICHLOROPROPANE
    PETROV, AD
    SADYKHZADE, SI
    TZETLIN, IL
    DOKLADY AKADEMII NAUK SSSR, 1956, 107 (01): : 99 - 102
12345