Ruthenium-Catalyzed 1,3-Aryl Redox Isomerization of Allylic Alcohols

被引：12

作者：

Luo, Zhen ^{[1
]}

Zhang, Xue ^{[1
]}

Liu, Zheng-Qiang ^{[1
]}

Hong, Chuan-Ming ^{[1
]}

Li, Qing-Hua ^{[1
]}

Liu, Tang-Lin ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

来源：

ORGANIC LETTERS | 2022年

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE ISOMERIZATION; TRANSFER HYDROGENATION; 1,2-ARYL MIGRATION; COMPLEXES; TRIFLUOROMETHYLATION; MECHANISM; OXIDATION; KETONES; WATER;

D O I：

10.1021/acs.orglett.2c03410

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isomerization of allylic alcohols to the corresponding carbonyl compounds is a well-established reaction in organic synthesis. However, 1,3-carbon migration is a quite challenging field, and thus transformation has remained elusive until now. Herein, we present the ruthenium-catalyzed intra-molecular 1,3-aryl migrative isomerization, which provides a mild and environmentally friendly method to synthesize various ketones with high step-and atom-economy and broad substrate scope. Meanwhile, the Ru(III)-catalyzed C(sp3)-C(aryl) bond cleavage of unactivated allylic alcohols may serve as a heuristic paradigm for transition-metal-catalyzed C-C activation.

引用

页码：8072 / 8076

页数：5

共 50 条

[21] ON THE MECHANISM OF THE RUTHENIUM-CATALYZED RECONSTITUTIVE CONDENSATION OF ALLYLIC ALCOHOLS AND TERMINAL ALKYNES
TROST, BM
KULAWIEC, RJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5579 - 5584
[22] Efficient redox isomerization of allylic alcohols under mild conditions catalyzed by arene-ruthenium(II) complexes
Crochet, Pascale
Fernandez-Zumel, Mariano A.
Gimeno, Jose
Scheele, Marcus
ORGANOMETALLICS, 2006, 25 (20) : 4846 - 4849
[23] Ruthenium-Catalyzed Stereoselective Allylic Substitutions
Kawatsura, Motoi
Minakawa, Maki
Itoh, Toshiyuki
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (01) : 45 - 55
[24] A stereospecific ruthenium-catalyzed allylic alkylation
Trost, BM
Fraisse, PL
Ball, ZT
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (06) : 1059 - +
[25] Ruthenium-catalyzed 1,3-dipolar cycloaddition of trifluoromethylated propargylic alcohols with azides
Zhang, Chun-Tao
Zhang, Xingang
Qing, Feng-Ling
TETRAHEDRON LETTERS, 2008, 49 (24) : 3927 - 3930
[26] Ruthenium-catalyzed reduction of allylic alcohols using glycerol as solvent and hydrogen donor
Diaz-Alvarez, Alba E.
Crochet, Pascale
Cadierno, Victorio
CATALYSIS COMMUNICATIONS, 2011, 13 (01) : 91 - 96
[27] Ruthenium-catalyzed allylic substitution of allylic cyclic carbonates
Kang, SK
Kim, DY
Hong, RK
Ho, PS
SYNTHETIC COMMUNICATIONS, 1996, 26 (17) : 3225 - 3235
[28] Ruthenium-Catalyzed Regio- and Enantioselective Allylic Substitution with Water: Direct Synthesis of Chiral Allylic Alcohols
Kanbayashi, Naoya
Onitsuka, Kiyotaka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5197 - 5199
[29] Ruthenium-Catalyzed One-Pot Tandem Isomerization-Transfer Hydrogenation Reactions of γ-Trifluoromethylated Allylic Alcohols and β-Trifluoromethylated Enones
Bizet, Vincent
Pannecoucke, Xavier
Renaud, Jean-Luc
Cahard, Dominique
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1394 - 1402
[30] Highly selective methanesulfonic acid-catalyzed 1,3-isomerization of allylic alcohols
Leleti, Rajender Reddy
Bin Hu
Prashad, Mahavir
Repic, Jan
TETRAHEDRON LETTERS, 2007, 48 (48) : 8505 - 8507

← 1 2 3 4 5 →