The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications

被引：299
作者：
Giustra, Zachary X. [1 ]
Liu, Shih-Yuan [1 ]
机构：
[1] Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 04期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
LATE-STAGE FUNCTIONALIZATION; RING-EXPANSION REACTION; HETEROAROMATIC-COMPOUNDS; B-N; BROMINATED 2,1-BORAZARONAPHTHALENES; CROSS-COUPLINGS; AZO DYES; C-C; BOROLES; NAPHTHALENE;
D O I：
10.1021/jacs.7b09446
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Boron-nitrogen heteroarenes hold great promise for practical application in many areas of chemistry. Enduring interest in realizing this potential has in turn driven perennial innovation with respect to these compounds' synthesis. This Perspective discusses in detail the most recent advances in methods pertaining to the preparation of BN-isosteres of benzene, naphthalene, and their derivatives. Additional focus is placed on the progress enabled by these syntheses toward functional utility of such BN-heterocycles in biochemistry and pharmacology, materials science, and transition-metal-based catalysis. The prospects for future research efforts in these and related fields are also assessed.
引用
收藏
页码：1184 / 1194
页数：11
相关论文
共 83 条
  • [51] Maus M. H., 2010, J PHYS CHEM A, V114, P2644
  • [52] Synthesis and Characterization of 1,2-Azaborine-Containing Phosphine Ligands: A Comparative Electronic Structure Analysis
    McConnell, Cameron R.
    Campbell, Patrick G.
    Fristoe, Carey R.
    Memmel, Philipp
    Zakharov, Lev N.
    Li, Bo
    Darrigan, Clovis
    Chrostowska, Anna
    Liu, Shih-Yuan
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (15) : 2207 - 2210
  • [53] Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2,1-borazaronaphthalenes
    Molander, Gary A.
    Amani, Javad
    Wisniewski, Steven R.
    [J]. ORGANIC LETTERS, 2014, 16 (22) : 6024 - 6027
  • [54] Suzuki-Miyaura Cross-Coupling of Brominated 2,1-Borazaronaphthalenes with Potassium Alkenyltrifluoroborates
    Molander, Gary A.
    Wisniewski, Steven R.
    Etemadi-Davan, Elharn
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (22) : 11199 - 11204
  • [55] Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethy1-2,1-borazaronaphthalene
    Molander, Gary A.
    Wisniewski, Steven R.
    Amani, Javad
    [J]. ORGANIC LETTERS, 2014, 16 (21) : 5636 - 5639
  • [56] Accessing 2,1-Borazaronaphthols: Self-Arylation of 1-Alkyl-2-aryl-3-bromo-2,1-borazaronaphthalenes
    Molander, Gary A.
    Wisniewski, Steven R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) : 8339 - 8347
  • [57] Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides
    Molander, Gary A.
    Wisniewski, Steven R.
    Traister, Kaitlin M.
    [J]. ORGANIC LETTERS, 2014, 16 (14) : 3692 - 3695
  • [58] Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki-Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates
    Molander, Gary A.
    Wisniewski, Steven R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) : 6663 - 6678
  • [59] Efficient synthetic methods for the installation of boron-nitrogen bonds in conjugated organic molecules
    Morgan, Matthew M.
    Piers, Warren E.
    [J]. DALTON TRANSACTIONS, 2016, 45 (14) : 5920 - 5924
  • [60] Charge-Transfer-Induced Magic Cluster Formation of Azaborine Heterocycles on Noble Metal Surfaces
    Murphy, Colin J.
    Miller, Daniel P.
    Simpson, Scott
    Baggett, Andrew
    Pronschinske, Alex
    Liriano, Melissa L.
    Therrien, Andrew J.
    Enders, Axel
    Liu, Shih-Yuan
    Zurek, Eva
    Sykes, E. Charles H.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2016, 120 (11) : 6020 - 6030
123456789