Palladium(II)-Catalyzed Aerobic 1,2-Diacetoxylation of Conjugated Dienes

被引：6

作者：

Ju, Chenyang ^{[1
]}

Wu, Zhengxing ^{[1
]}

Li, Yunyi ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn & Chiral Drugs, Shanghai 200240, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 40卷 / 11期

基金：

中国国家自然科学基金;

关键词：

palladium; conjugated diene; 1,2-diacetoxylation; 1,2-diol; ALPHA-AMINO-ACIDS; ALLYLIC SUBSTITUTION CASCADE; IR/ZN DUAL CATALYSIS; MOLECULAR-OXYGEN; INTERMOLECULAR 1,2-DIAMINATION; DIASTEREODIVERGENT ACCESS; NATURAL-PRODUCTS; BOND FORMATION; 1,3-DIENES; ALKENES;

D O I：

10.6023/cjoc202004025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Diols have important applications in pesticides, chiral medicines and fine chemicals. A Pd(II)-catalyzed 1,2-diacetoxylation method using readily available acetic acid as the oxygen source and oxygen as the oxidant was developed. For the 1,2-diacetoxylation of conjugated dienes, the reaction proceeds with high 1,2-regioselectivity. This protocol has good substrate scope for conjugated dienes possessing aryl-, ester- and carbonyl groups. The catalytic products can be transformed to 1,2-diols through simple alcoholysis or hydrolysis, therefore it is an efficient method for the synthesis of 1,2-diols.y

引用

页码：3925 / 3933

页数：9

共 86 条

[1] Palladium-catalyzed 1,4-acetoxy-trifluoroacetoxylation and 1,4-alkoxy-trifluoroacetoxylation of cyclic 1,3-dienes.: Scope and mechanism [J].

Aranyos, A ;

Szabó, KJ ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2523-2529

[2]

Backvall J.-E., 2004, MET CATAL CROSS COUP, V2, P479

[3]

Backvall J.-E., 1992, J AM CHEM SOC, V114, P6374

[4] Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].

Bar, GLJ ;

Lloyd-Jones, GC ;

Booker-Milburn, KI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309

[5] Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes [J].

Bhowmik, Amit ;

Fernandes, Rodney A. .

ORGANIC LETTERS, 2019, 21 (22) :9203-9207

[6] POTENTIAL INHIBITORS OF S-ADENOSYLMETHIONINE-DEPENDENT METHYLTRANSFERASES .11. MOLECULAR DISSECTIONS OF NEPLANOCIN-A AS POTENTIAL INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE [J].

BORCHERDING, DR ;

NARAYANAN, S ;

HASOBE, M ;

MCKEE, JG ;

KELLER, BT ;

BORCHARDT, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1729-1738

[7] Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration [J].

Burks, Heather E. ;

Kliman, Laura T. ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) :9134-+

[8] Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].

Campbell, Alison N. ;

Stahl, Shannon S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863

[9] Palladium-Catalyzed Cascade sp2 C-H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3-Dienes to Chiral Indolines [J].

Chen, Shu-Sen ;

Wu, Min-Song ;

Han, Zhi-Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (23) :6641-6645

[10] A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation [J].

Cooper, Stephen P. ;

Booker-Milburn, Kevin I. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) :6496-6500

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