Rhodium-catalyzed synthesis of 1-silabenzonorbornenes via 1,4-rhodium migration

被引：0
|
作者：
Shintani, Ryo [1 ,2 ]
Hama, Daichi [1 ]
Hamada, Naoya [1 ]
Miwa, Takuya [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn Sci, Dept Mat Engn Sci, Div Chem, Toyonaka, Osaka 5608531, Japan
[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTR, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan
来源：
TETRAHEDRON LETTERS | 2022年 / 104卷
关键词：
1,4-Rhodium migration; Silicon switch; Silabenzonorbornene; Organoboron reagent; ASYMMETRIC 1,4-ADDITION; SILICON ISOSTERES; ARYLBORONIC ACIDS; DESIGN; CHALLENGES; CHEMISTRY; REAGENTS; COMPLEX; CASCADE; ALKYNES;
D O I：
10.1016/j.tetlet.2022.154031
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of 1-silabenzonorbornenes was developed from a simple substrate combination of alkynyl(2-alkylallyl)silanes and arylboron reagents under rhodium catalysis through the use of 1,4-rhodium migration. Three carbon-carbon bonds were newly formed during the catalytic process and the reaction pathway was probed by a deuterium labeling experiment as well. (C) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [1] Rhodium-Catalyzed Synthesis of Silicon-Bridged 1,2-Dialkenylbenzenes via 1,4-Rhodium Migration
    Miwa, Takuya
    Shintani, Ryo
    ORGANIC LETTERS, 2019, 21 (06) : 1627 - 1631
  • [2] Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration
    O'Brien, Luke
    Karad, Somnath Narayan
    Lewis, William
    Lam, Hon Wai
    CHEMICAL COMMUNICATIONS, 2019, 55 (76) : 11366 - 11369
  • [3] Rhodium-Catalyzed Polymerization of 3,3-Diarylcyclopropenes Involving a 1,4-Rhodium Migration
    Shintani, Ryo
    Iino, Ryo
    Nozaki, Kyoko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) : 7849 - 7852
  • [4] Rhodium-catalyzed polymerization of 3,3-diarylcyclopropenes involving a 1,4-rhodium migration
    Shintani, R. (shintani@chembio.t.u-tokyo.ac.jp), 1600, American Chemical Society (136):
  • [5] Rhodium-Catalyzed Expeditious Synthesis of Indenes from Propargyl Alcohols and Organoboronic Acids by Selective 1,4-Rhodium Migration over β-Oxygen Elimination
    Liu, Na
    Yao, Jian
    Yin, Long
    Lu, Tao
    Tian, Ziqi
    Dou, Xiaowei
    ACS CATALYSIS, 2019, 9 (08): : 6857 - 6863
  • [6] Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration
    Callingham, Michael
    Partridge, Benjamin M.
    Lewis, William
    Lam, Hon Wai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) : 16352 - 16356
  • [7] Chemodivergent Oxidative Annulation of Benzamides and Enynes via 1,4-Rhodium Migration
    Sun, Jiaqiong
    Bai, Dachang
    Wang, Peiyuan
    Wang, Kuan
    Zheng, Guangfan
    Li, Xingwei
    ORGANIC LETTERS, 2019, 21 (06) : 1789 - 1793
  • [8] Aryloxymethyltrifluoroborates for Rhodium-Catalyzed Asymmetric Conjugate Arylation. o-Methoxyarylation through 1,4-Rhodium Shift
    Ming, Jialin
    Hayashi, Tamio
    ORGANIC LETTERS, 2016, 18 (24) : 6452 - 6455
  • [9] Rhodium-catalyzed 1,4-hydroxyl migration of alkenyl alcohols
    Zhang, Xue
    Yan, Jiang-Min
    Zhang, Jia-Ning
    Xiong, Si-Qi
    Liang, Cheng
    Li, Qing-Hua
    Liu, Tang-Lin
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (19): : 5368 - 5373
  • [10] Rhodium(III)-Catalyzed [4+1] Oxidative Annulation of Amides with 1,3-enynes Through 1,4-Rhodium Migration
    Reddy, Chada Raji
    Subbarao, Muppidi
    Rathaur, Anjali
    Srinivasu, Ejjirotu
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) : 2036 - 2042
12345