C-H Bond activation by alumina:: facile hydroxylation of chlorins at their saturated β-carbon by molecular oxygen and alumina

被引：17

作者：

Burns, DH ^{[1
]}

Li, YH ^{[1
]}

Shi, DC ^{[1
]}

Delaney, MO ^{[1
]}

机构：

[1] Wichita State Univ, Dept Chem, Wichita, KS 67260 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 16期

关键词：

D O I：

10.1039/a802165a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The mono-hydroxylation of a beta-methylene carbon in the pyrroline ring of a chlorin requires only alumina and molecular oxygen as reagents, with good yields (70-80%) of the hydroxy chlorin obtained at room temperature in 2 h; this is the first example of a hydroxylated chlorin that has been prepared in a regiospecific manner starting from a chlorin, and the first demonstration of the mild activation of a C-H bond by alumina for its oxidation into a hydroxy group.

引用

收藏

页码：1677 / 1678

页数：2

相关论文

共 13 条

[1]

ANDERSSON LA, 1984, J BIOL CHEM, V259, P5340

[2] FACILE LACTONIZATION AND INVERSION OF VICINAL DIOLS IN HEME D-TYPE CHLORINS - A SPECTROSCOPIC STUDY [J].

ANDERSSON, LA ;

SOTIRIOU, C ;

CHANG, CK ;

LOEHR, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) :258-264

[3] MOLECULAR-STRUCTURE OF A DIHYDROXYCHLORIN - A MODEL OF THE GREEN HEME-D AND OF A PHOTODYNAMIC THERAPY SENSITIZER [J].

BARKIGIA, KM ;

CHANG, CK ;

FAJER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7445-7447

[4] A RATIONAL STEP-BY-STEP PREPARATION OF A CHLORIN FROM LINEAR TETRAPYRROLES [J].

BURNS, DH ;

CALDWELL, TM ;

BURDEN, MW .

TETRAHEDRON LETTERS, 1993, 34 (18) :2883-2886

[5]

HYNNINEN PH, 1991, CHLOROPHYLLS, P176

[6] DISCOVERY AND SYNTHESIS OF LESS COMMON NATURAL HYDROPORPHYRINS [J].

MONTFORTS, FP ;

GERLACH, B ;

HOPER, F .

CHEMICAL REVIEWS, 1994, 94 (02) :327-347

[7] PREPARATION AND CHARACTERIZATION OF OXOIRON(IV) CHLORIN COMPLEXES AS THE 1ST MODELS FOR A REACTION INTERMEDIATE IN THE CATALYTIC CYCLE OF CYTOCHROME-D [J].

OZAWA, S ;

WATANABE, Y ;

NAKASHIMA, S ;

KITAGAWA, T ;

MORISHIMA, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :634-641

[8] ORGANIC-REACTIONS AT ALUMINA SURFACES [J].

POSNER, GH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07) :487-496

[9] Catalytic activities of CuSO4/Al2O3 in dehydrogenation of arenes by dioxygen [J].

Sakamoto, T ;

Yonehara, H ;

Pac, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3194-3199

[10] SULFMYOGLOBIN DERIVED FROM DEUTEROHEMIN RECONSTITUTED PROTEIN .1. STRUCTURE OF THE INITIAL COMPLEX BASED ON THE MECHANISM OF FORMATION OF SUBSEQUENT REACTION-PRODUCTS [J].

SCHARBERG, MA ;

LAMAR, GN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6513-6521