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

被引:318
作者
Giustra, Zachary X. [1 ]
Liu, Shih-Yuan [1 ]
机构
[1] Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
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 [J].
McConnell, Cameron R. ;
Campbell, Patrick G. ;
Fristoe, Carey R. ;
Memmel, Philipp ;
Zakharov, Lev N. ;
Li, Bo ;
Darrigan, Clovis ;
Chrostowska, Anna ;
Liu, Shih-Yuan .
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 [J].
Molander, Gary A. ;
Amani, Javad ;
Wisniewski, Steven R. .
ORGANIC LETTERS, 2014, 16 (22) :6024-6027
[54]   Suzuki-Miyaura Cross-Coupling of Brominated 2,1-Borazaronaphthalenes with Potassium Alkenyltrifluoroborates [J].
Molander, Gary A. ;
Wisniewski, Steven R. ;
Etemadi-Davan, Elharn .
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 [J].
Molander, Gary A. ;
Wisniewski, Steven R. ;
Amani, Javad .
ORGANIC LETTERS, 2014, 16 (21) :5636-5639
[56]   Accessing 2,1-Borazaronaphthols: Self-Arylation of 1-Alkyl-2-aryl-3-bromo-2,1-borazaronaphthalenes [J].
Molander, Gary A. ;
Wisniewski, Steven R. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8339-8347
[57]   Reductive Cross-Coupling of 3-Bromo-2,1-borazaronaphthalenes with Alkyl Iodides [J].
Molander, Gary A. ;
Wisniewski, Steven R. ;
Traister, Kaitlin M. .
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 [J].
Molander, Gary A. ;
Wisniewski, Steven R. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) :6663-6678
[59]   Efficient synthetic methods for the installation of boron-nitrogen bonds in conjugated organic molecules [J].
Morgan, Matthew M. ;
Piers, Warren E. .
DALTON TRANSACTIONS, 2016, 45 (14) :5920-5924
[60]   Charge-Transfer-Induced Magic Cluster Formation of Azaborine Heterocycles on Noble Metal Surfaces [J].
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. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2016, 120 (11) :6020-6030