Metal-free nitro-carbocyclization of 1,6-enynes with tBuONO and TEMPO

被引：74

作者：

Hao, Xin-Hua ^{[1
]}

Gao, Pin ^{[1
]}

Song, Xian-Rong ^{[1
]}

Qiu, Yi-Feng ^{[1
]}

Jin, Dong-Po ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 31期

基金：

美国国家科学基金会;

关键词：

TERT-BUTYL NITRITE; STEREOSELECTIVE NITRATION; CONJUGATED NITROALKENES; AEROBIC OXYNITRATION; ALKENES; ALKYNES; OLEFINS; OXIDATION; ENYNES; FUNCTIONALIZATION;

D O I：

10.1039/c5cc00872g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and convenient metal-free nitration and cyclization of 1,6-enynes has been developed. Two C-C bonds and one C-N bond were constructed in one process in this reaction. This transformation is proven to have relatively good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. According to the following experimental facts and related literature reports, a radical pathway was involved in this transformation.

引用

页码：6839 / 6842

页数：4

共 61 条

[1]

[Anonymous], CHEMTRACTS

[2] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[3] NITRATION STUDIES .15. NITROMERCURATION AND SYNTHESIS OF BETA-NITROMERCURIALS [J].

BACHMAN, GB ;

WHITEHOU.ML .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (07) :2303-+

[4] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

BARRETT, AGM ;

GRABOSKI, GG .

CHEMICAL REVIEWS, 1986, 86 (05) :751-762

[5] PHOTOCHEMICAL NITRATION BY TETRANITROMETHANE .18. THE REGIOCHEMISTRY OF NITRITO TRINITROMETHYL AND NITRO/TRINITROMETHYL ADDITION TO 2,3-DIMETHYLNAPHTHALENE - THERMAL 1,3-DIPOLAR ADDITIONS OF NITRO-GROUPS TO ALKENES [J].

BUTTS, CP ;

CALVERT, JL ;

EBERSON, L ;

HARTSHORN, MP ;

RADNER, F ;

ROBINSON, WT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (07) :1485-1490

[6] One-pot selective synthesis of β-nitrostyrenes from styrenes, promoted by Cu(II) [J].

Campos, PJ ;

García, B ;

Rodríguez, MA .

TETRAHEDRON LETTERS, 2000, 41 (06) :979-982

[7] NEW SYNTHESIS OF CONJUGATED NITRO CYCLO OLEFINS, UNUSUALLY VERSATILE SYNTHETIC INTERMEDIATES [J].

COREY, EJ ;

ESTREICHER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6294-6295

[8] Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles [J].

Deng, Guo-Bo ;

Zhang, Jia-Ling ;

Liu, Yan-Yun ;

Liu, Bang ;

Yang, Xu-Heng ;

Li, Jin-Heng .

CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1886-1888

[9] Aerobic Oxynitration of Alkynes with tBuONO and TEMPO [J].

Dutta, Uttarn ;

Maity, Soham ;

Kancherla, Rajesh ;

Maiti, Debabrata .

ORGANIC LETTERS, 2014, 16 (24) :6302-6305

[10] PEROXYTRIFLUOROACETIC ACID .6. THE OXIDATION OF OXIMES TO NITROPARAFFINS [J].

EMMONS, WD ;

PAGANO, AS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (17) :4557-4559

← 1 2 3 4 5 6 7 →