Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes

被引：48

作者：

Yang, Jun ^{[1
,2
]}

Ji, Ding-Wei ^{[2
]}

Hu, Yan-Cheng ^{[2
]}

Min, Xiang-Ting ^{[2
]}

Zhou, Xiangge ^{[1
]}

Chen, Qing-An ^{[2
]}

机构：

[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Chengdu 610064, Sichuan, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 41期

基金：

中国国家自然科学基金;

关键词：

CARBON QUATERNARY CENTERS; C BOND FORMATION; ENANTIOSELECTIVE SYNTHESIS; H ACTIVATION; ALLYLATION; 1,3-DIENES; ALCOHOLS; HYDROHYDROXYALKYLATION; CRYPTOPHYCINS; ALDEHYDES;

D O I：

10.1039/c9sc03747k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Terpenes, consisting of isoprene monomer units, represent a family of naturally abundant compounds. The difunctionalization of terpenes is highly appealing yet remains challenging, since the multiple unbiased C=C bonds of terpenes lead to difficulty in controlling the regioselectivity. Herein, a cobalt(iii)-catalyzed C-H activation strategy has been developed to facilitate hydroxymethylarylation of terpenes with formaldehyde and arenes with high chemo- and regio-selectivities. These (chemo- and regio-) selectivities are governed by the coordination abilities of isoprene, directing groups and the steric effect. This terpene difunctionalization also features high atom and step economy through a C-H addition pathway.

引用

页码：9560 / 9564

页数：5

共 70 条

[51] Paraformaldehyde and Methanol as C1 Feedstocks in Metal-Catalyzed C-C Couplings of π-Unsaturated Reactants: Beyond Hydroformylation [J].

Sam, Brannon ;

Breit, Bernhard ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (11) :3267-3274

[52] Ruthenium-catalyzed C-C bond forming transfer hydrogenation: Carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents [J].

Shibahara, Fumitoshi ;

Bower, John F. ;

Krische, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6338-+

[53] All-Carbon Quaternary Centers via Ruthenium-Catalyzed Hydroxymethylation of 2-Substituted Butadienes Mediated by Formaldehyde: Beyond Hydroformylation [J].

Smejkal, Tomas ;

Han, Hoon ;

Breit, Bernhard ;

Krische, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10366-+

[54] Direct C-H Transformation via Iron Catalysis [J].

Sun, Chang-Liang ;

Li, Bi-Jie ;

Shi, Zhang-Jie .

CHEMICAL REVIEWS, 2011, 111 (03) :1293-1314

[55] Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII-Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls [J].

Sun Dongbang ;

Shen, Zican ;

Ellman, Jonathan A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (36) :12590-12594

[56] TOTAL STRUCTURES OF CRYPTOPHYCINS, POTENT ANTITUMOR DEPSIPEPTIDES FROM THE BLUE-GREEN-ALGA NOSTOC SP STRAIN GSV-224 [J].

TRIMURTULU, G ;

OHTANI, I ;

PATTERSON, GML ;

MOORE, RE ;

CORBETT, TH ;

VALERIOTE, FA ;

DEMCHIK, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4729-4737

[57] Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches [J].

Trost, Barry M. ;

Dong, Guangbin .

NATURE, 2008, 456 (7221) :485-488

[58] Epoxide-opening cascades promoted by water [J].

Vilotijevic, Ivan ;

Jamison, Timothy F. .

SCIENCE, 2007, 317 (5842) :1189-1192

[59] Rh(III)-Catalyzed Regioselective Acetylation of sp2 C-H Bond Starting from Paraformaldehyde [J].

Wan, Ting ;

Du, Sidong ;

Pi, Chao ;

Wang, Yong ;

Li, Rongbin ;

Wu, Yangjie ;

Cui, Xiuling .

CHEMCATCHEM, 2019, 11 (16) :3791-3796

[60] Towards mild metal-catalyzed C-H bond activation [J].

Wencel-Delord, Joanna ;

Droege, Thomas ;

Liu, Fan ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4740-4761

← 1 2 3 4 5 6 7 →