4-(Dimethylamino)pyridine (DMAP) as an Acid-Modulated Donor Ligand for PAH Dearomatization

被引：12

作者：

Myers, Jeffery T. ^{[1
]}

Dakermanji, Steven J. ^{[1
]}

Chastanet, Timothy R. ^{[1
]}

Shivokevich, Philip J. ^{[1
]}

Strausberg, Laura J. ^{[1
]}

Sabat, Michal ^{[1
]}

Myers, William H. ^{[2
]}

Harman, W. Dean ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

[2] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

来源：

ORGANOMETALLICS | 2017年 / 36卷 / 03期

基金：

美国国家科学基金会;

关键词：

PI-BASE; TUNGSTEN; NAPHTHALENE; COMPLEXES; AGENTS; OSMIUM(II); CHEMISTRY;

D O I：

10.1021/acs.organomet.6b00780

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The dearomatization of naphthalene and anthracene is explored by their eta(2) coordination to {TpMo(NO)(MeIm)} and {TpMo(NO)(DMAP)} (where Tp = hydridotris(pyrazolyl)borate, MeIm = 1-methylimidazole, and DMAP = 4-(dimethylamino)pyridine). The DMAP and MeIm complexes have nearly identical redox properties and abilities to bind these polycyclic aromatic hydrocarbons (PAHs), but unlike MeIm, the DMAP ligand can be protonated at N while remaining bound to the metal. This action enhances the pi- acidic properties of DMAP, resulting in greater stability of the molybdenum toward oxidation by acid. Utilizing this feature of.the DMAP ligand, several new 1,2-dihydronaphthalenes and 1,2-dihydroanthracenes were prepared. Furthermore, it was found that acetals and Michael acceptors could function as electrophiles for the PAHs using the DMAP system, resulting in several new mono- and 1,4-dialkylated products.

引用

页码：543 / 555

页数：13

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