A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position

被引：30

作者：

Abengozar, Alberto ^{[1
]}

Sucunza, David ^{[1
]}

Garcia-Garcia, Patricia ^{[1
]}

Sampedro, Diego ^{[2
]}

Perez-Redondo, Adrian ^{[1
]}

Vaquero, Juan J. ^{[1
]}

机构：

[1] Univ Alcala, Dept Quim Organ & Quim Inorgan, Inst Invest Quim Andres M del Rio IQAR, Alcala De Henares 28805, Spain

[2] Univ La Rioja, Dept Quim, CISQ, Madre Dios 53, Logrono 26006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 11期

关键词：

AROMATIC-SUBSTITUTION REACTIONS; HETEROAROMATIC-COMPOUNDS; SYNTHETIC METHODS; C-C; 2,1-BORAZARONAPHTHALENES; NAPHTHALENE; AZABORINES;

D O I：

10.1021/acs.joc.9b00800

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all nonsubstituted BN-phenanthrenes reported to date (phi(F) = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds toward organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.

引用

页码：7113 / 7122

页数：10

共 46 条

[1] Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives [J].

Abengozar, Alberto ;

Garcia-Garcia, Patricia ;

Sucunza, David ;

Sampedro, Diego ;

Perez-Reclondo, Adrian ;

Vaquero, Juan J. .

ORGANIC LETTERS, 2019, 21 (08) :2550-2554

[2] C-H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom [J].

Abengozar, Alberto ;

Angel Fernandez-Gonzalez, Miguel ;

Sucunza, David ;

Manuel Frutos, Luis ;

Salgado, Antonio ;

Garcia-Garcia, Patricia ;

Vaquero, Juan J. .

ORGANIC LETTERS, 2018, 20 (16) :4902-4906

[3] Synthesis of functionalized helical BN-benzo[c]phenanthrenes [J].

Abengozar, Alberto ;

Garcia-Garcia, Patricia ;

Sucunza, David ;

Perez-Redondo, Adrian ;

Vaquero, Juan J. .

CHEMICAL COMMUNICATIONS, 2018, 54 (20) :2467-2470

[4] Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene [J].

Abengozar, Alberto ;

Garcia-Garcia, Patricia ;

Sucunza, David ;

Manuel Frutos, Luis ;

Castano, Obis ;

Sampedro, Diego ;

Perez-Redondo, Adrian ;

Vaquero, Juan J. .

ORGANIC LETTERS, 2017, 19 (13) :3458-3461

[5] 2ND-ORDER PERTURBATION-THEORY WITH A COMPLETE ACTIVE SPACE SELF-CONSISTENT FIELD REFERENCE FUNCTION [J].

ANDERSSON, K ;

MALMQVIST, PA ;

ROOS, BO .

JOURNAL OF CHEMICAL PHYSICS, 1992, 96 (02) :1218-1226

[6] Molcas 8: New capabilities for multiconfigurational quantum chemical calculations across the periodic table [J].

Aquilante, Francesco ;

Autschbach, Jochen ;

Carlson, Rebecca K. ;

Chibotaru, Liviu F. ;

Delcey, Mickael G. ;

De Vico, Luca ;

Galvan, Ignacio Fdez ;

Ferre, Nicolas ;

Frutos, Luis Manuel ;

Gagliardi, Laura ;

Garavelli, Marco ;

Giussani, Angelo ;

Hoyer, Chad E. ;

Li Manni, Giovanni ;

Lischka, Hans ;

Ma, Dongxia ;

Malmqvist, Per Ake ;

Mueller, Thomas ;

Nenov, Artur ;

Olivucci, Massimo ;

Pedersen, Thomas Bondo ;

Peng, Daoling ;

Plasser, Felix ;

Pritchard, Ben ;

Reiher, Markus ;

Rivalta, Ivan ;

Schapiro, Igor ;

Segarra-Marti, Javier ;

Stenrup, Michael ;

Truhlar, Donald G. ;

Ungur, Liviu ;

Valentini, Alessio ;

Vancoillie, Steven ;

Veryazov, Valera ;

Vysotskiy, Victor P. ;

Weingart, Oliver ;

Zapata, Felipe ;

Lindh, Roland .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2016, 37 (05) :506-541

[7] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[8] Recent Developments in Azaborinine Chemistry [J].

Belanger-Chabot, Guillaume ;

Braunschweig, Holger ;

Roy, Dipak Kumar .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (38-39) :4353-4368

[9] Blue fluorescent 4a-aza-4b-boraphenanthrenes [J].

Bosdet, Michael J. D. ;

Jaska, Cory A. ;

Piers, Warren E. ;

Sorensen, Ted S. ;

Parvez, Masood .

ORGANIC LETTERS, 2007, 9 (07) :1395-1398

[10] B-N as a C-C substitute in aromatic systems [J].

Bosdet, Michael J. D. ;

Piers, Warren E. .

CANADIAN JOURNAL OF CHEMISTRY, 2009, 87 (01) :8-29

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