Azido-alkynylation of alkenes through radical-polar crossover

被引：11
作者：
Borrel, Julien [1 ]
Waser, Jerome [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Catalysis & Organ Synth, EPFL SB IS LCSO, BCH 4306, CH-1015 Lausanne, Switzerland
来源：
CHEMICAL SCIENCE | 2023年 / 14卷 / 35期
基金：
瑞士国家科学基金会;
关键词：
TRANSITION-METAL-FREE; DECARBOXYLATIVE ALKYNYLATION; CLICK CHEMISTRY; ALPHA; ALPHA-DIFLUOROARYLACETIC ACIDS; ENANTIOSELECTIVE SYNTHESIS; STABLE AZIDOIODINANES; ORGANIC AZIDES; AZIDATION; PYRROLE; DERIVATIVES;
D O I：
10.1039/d3sc03309k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process was key to develop this transformation. A variety of homopropargylic azides possessing electron-rich and -poor aryls, heterocycles or ether substituents could be accessed in 34-84% yield. The products are synthetically useful building blocks that could be easily transformed into pyrroles or bioactive amines.
引用
收藏
页码：9452 / 9460
页数：9
相关论文
共 120 条
  • [1] Pyrrole: An insight into recent pharmacological advances with structure activity relationship
    Ahmad, Shujauddin
    Alam, Ozair
    Naim, Mohd. Javed
    Shaquiquzzaman, Mohammad
    Alam, M. Mumtaz
    Iqbal, Muzaffar
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 157 : 527 - 561
  • [2] Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
    Alazet, Sebastien
    Preindl, Johannes
    Simonet-Davin, Raphael
    Nicolai, Stefano
    Nanchen, Annik
    Meyer, Thierry
    Waser, Jerome
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) : 12334 - 12356
  • [3] Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents
    Alazet, Sebastien
    Le Vaillant, Franck
    Nicolai, Stefano
    Courant, Thibaut
    Waser, Jerome
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (40) : 9501 - 9504
  • [4] A well feasible and general route to (organoethynyl)difluoroboranes, RHC≡CBF2, and their perfluorinated analogues, RFC≡CBF2
    Bardin, Vadim V.
    Adonin, Nicolay Yu.
    Frohn, Hermann-Josef
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (07) : 699 - 702
  • [5] Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics
    Bhardwaj, Varun
    Gumber, Divya
    Abbot, Vikrant
    Dhiman, Saurabh
    Sharma, Poonam
    [J]. RSC ADVANCES, 2015, 5 (20): : 15233 - 15266
  • [6] Gold-Catalyzed Oxidative Alkyne Functionalization by N-O/S-O/C-O Bond Oxidants
    Bhunia, Sabyasachi
    Ghosh, Partha
    Patra, Snigdha Rani
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (18) : 3664 - 3708
  • [7] Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations
    Borrel, Julien
    Waser, Jerome
    [J]. ORGANIC LETTERS, 2022, 24 (01) : 142 - 146
  • [8] Addition of Trifluoroborates to Oxetanyl N,O-Acetals: Entry into Spiro and Fused Saturated Heterocycles
    Brady, Patrick B.
    Carreira, Erick M.
    [J]. ORGANIC LETTERS, 2015, 17 (13) : 3350 - 3353
  • [9] Organic azides:: An exploding diversity of a unique class of compounds
    Bräse, S
    Gil, C
    Knepper, K
    Zimmermann, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
  • [10] Brase S., 2009, Organic Azides: Syntheses and Applications
12345678910