Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds

被引：56
|
作者：
Stephens, Thomas C. [1 ]
Pattison, Graham [1 ]
机构：
[1] Univ Warwick, Dept Chem, Gibbet Hill Rd, Coventry CV4 7AL, W Midlands, England
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 13期
关键词：
HYDROXYL BORONIC ESTERS; ALLYLIC SUBSTITUTION; CARBONYL-COMPOUNDS; ARYLBORONIC ACIDS; ALKYL-HALIDES; DIASTEREOSELECTIVE SYNTHESIS; DEHYDROGENATIVE BORYLATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; GEM-SILYLBORYLATION;
D O I：
10.1021/acs.orglett.7b01474
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks. which provides the coupled, homologated carbonyl compound, upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces anew carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.
引用
收藏
页码：3498 / 3501
页数：4
相关论文
共 50 条
  • [21] Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
    Gerleve, Carolin
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (36) : 15468 - 15473
  • [22] A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids
    Ueda, Mitsuhiro
    Nishimura, Kota
    Kashima, Ryo
    Ryu, Ilhyong
    SYNLETT, 2012, (07) : 1085 - 1089
  • [23] Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines
    Li, Bin
    Chen, Zhiyu
    Cao, Hua
    Zhao, Hong
    ORGANIC LETTERS, 2018, 20 (11) : 3291 - 3295
  • [24] Oxidative Cross-Coupling of Alcohols and Amines Catalyzed by TEMPO under Transition-Metal-Free Condition
    Chandrasekaran, Revathi
    Carlose, Elgin
    Muthu, Ajun E.
    Suresh, Athira
    Chinnusamy, Tamilselvi
    CHEMISTRYSELECT, 2020, 5 (21): : 6285 - 6293
  • [25] Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes
    Ueda, Mitsuhiro
    Nakakoji, Daiki
    Kuwahara, Yuki
    Nishimura, Kota
    Ryu, Ilhyong
    TETRAHEDRON LETTERS, 2016, 57 (37) : 4142 - 4144
  • [26] Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride
    Ieki, Ryosuke
    Kani, Yuria
    Tsunoi, Shinji
    Shibata, Ikuya
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (16) : 6295 - 6300
  • [27] Dehydrative Cross-Coupling for C-N Bond Construction under Transition-Metal-Free Conditions
    Xing, Huicong
    Chen, Meijuan
    Zhang, Dong
    Geng, Zhishuai
    Xie, Peizhong
    Loh, Teck-Peng
    ORGANIC LETTERS, 2022, 24 (31) : 5657 - 5662
  • [28] Transition-Metal-Free Cross-Coupling Reactions in Dynamic Thin Films To Access Pyrimidine and Quinoxaline Analogues
    Ho, Louisa A.
    Raston, Colin L.
    Stubbs, Keith A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (36) : 5957 - 5963
  • [29] Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones
    Jadhav, Sanjay
    Rashinkar, Gajanan
    Salunkhe, Rajashri
    Kumbhar, Arjun
    TETRAHEDRON LETTERS, 2017, 58 (33) : 3201 - 3204
  • [30] Transition-Metal-Free Cross-Coupling of Acetals and Grignard Reagents To Form Diarylmethyl Alkyl Ethers and Triarylmethanes
    Qin, Yang
    Liu, Sheng
    Shi, Shi-Liang
    SYNTHESIS-STUTTGART, 2024, 56 (04): : 527 - 538
12345