Late-Stage Functionalization of 1,2-Dihydro-1,2-azaborines via Regioselective Iridium-Catalyzed C-H Borylation: The Development of a New N,N-Bidentate Ligand Scaffold

被引：64

作者：

Baggett, Andrew W. ^{[1
,2
]}

Vasiliu, Monica ^{[3
]}

Li, Bo ^{[1
]}

Dixon, David A. ^{[3
]}

Liu, Shih-Yuan ^{[1
,2
]}

机构：

[1] Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA

[2] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA

[3] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 16期

基金：

美国国家科学基金会;

关键词：

AROMATIC-SUBSTITUTION REACTIONS; B-N; 1,2-AZABORINES; COMPLEXES; CONSTRUCTION; ACTIVATION; BIPYRIDINE; ARYLATION; INSIGHTS; DIBORON;

D O I：

10.1021/jacs.5b01916

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first general late-Stage functionalization of monocyclic. 1,2-azaborines at the C(6) position is described. Ir-catalyzed C-H borylation occurs regioselectively at the C(6) position of B-substituted 1,2-azaborines and is compatible with a range of substitution patterns at boron (e.g., hydride, alkoxide, alkyl, and aryl substituents). Subsequent Suzuki cross coupling with aryl- and heteroaryl bromides furnishes, 1,2,azaborine-based-biaryl compounds including 6,-[pyrid-2-yl]-1,2-azaborines that represent novel kappa(2)-N,N-bidentate ligands. The 6-[pyrid-2-yl]-B-Me-1,2-azaborine ligand has been demonstrated. to form an emissive coordination complex with dimesitylboron that exhibits bathochromically shifted absorption and emission maxima, and a higher photoluminescence quantum yield compared to its carbonaceous analogue.

引用

页码：5536 / 5541

页数：6