Ruthenium Phosphine Pyridone Catalyzed Cross-Coupling of Alcohols To form α-Alkylated Ketones

被引：55

作者：

Sahoo, Apurba R. ^{[1
]}

Lalitha, Gummidi ^{[2
]}

Murugesh, V. ^{[2
]}

Bruneau, Christian ^{[1
]}

Sharma, Gangavaram V. M. ^{[2
]}

Suresh, Surisetti ^{[2
]}

Achard, Mathieu ^{[1
]}

机构：

[1] Univ Rennes 1, Inst Sci Chim Rennes, UMR 6226, Campus Beaulieu, F-35042 Rennes, France

[2] CSIR IICT, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期

关键词：

SECONDARY ALCOHOLS; BETA-ALKYLATION; BORROWING-HYDROGEN; BOND FORMATION; C-C; METAL-FREE; IRIDIUM; COMPLEXES; EFFICIENT; 2-METHYLENEAZIRIDINES;

D O I：

10.1021/acs.joc.7b02042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and green route to access diverse functionalized ketones via dehydrogenative-dehydrative cross-coupling of primary and secondary alcohols is demonstrated. Selective and tunable formation of ketones or alcohols is catalyzed by a recently developed proton responsive ruthenium phosphine pyridone complex. Light alcohols such as ethanol could be used as alkylating agents in this methodology. Moreover, selective tandem double alkylation of isopropanol is achieved by sequential addition of different alcohols.

引用

页码：10727 / 10731

页数：5

共 62 条

[11] Ruthenium and osmium complexes in C-C bond-forming reactions by borrowing hydrogen catalysis [J].

Chelucci, Giorgio .

COORDINATION CHEMISTRY REVIEWS, 2017, 331 :1-36

[12] A palladium-catalyzed route for α-alkylation of ketones by primary alcohols [J].

Cho, CS .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 240 (1-2) :55-60

[13]

Cho CS, 2005, B KOREAN CHEM SOC, V26, P1611

[14] Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols [J].

Cho, CS ;

Kim, BT ;

Kim, HS ;

Kim, TJ ;

Shim, SC .

ORGANOMETALLICS, 2003, 22 (17) :3608-3610

[15] Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols [J].

Cho, CS ;

Kim, BT ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2002, 43 (44) :7987-7989

[16] Efficient, Regioselective Palladium-Catalyzed Tandem Heck-Isomerization Reaction of Aryl Bromides and Non-Allylic Benzyl Alcohols [J].

Crawley, Matthew L. ;

Phipps, Kristin M. ;

Goljer, Igor ;

Mehlmann, John F. ;

Lundquist, Joseph T. ;

Ullrich, John W. ;

Yang, Cuijian ;

Mahaney, Paige E. .

ORGANIC LETTERS, 2009, 11 (05) :1183-1185

[17] General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols [J].

Deibl, Nicklas ;

Kempe, Rhett .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) :10786-10789

[18] Iron-Catalyzed α-Alkylation of Ketones with Alcohols [J].

Elangovan, Saravanakumar ;

Sortais, Jean-Baptiste ;

Beller, Matthias ;

Darcel, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14483-14486

[19] Cobalt-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer [J].

Freitag, Frederik ;

Irrgang, Torsten ;

Kempe, Rhett .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) :12110-12113

[20] Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as Electrophiles [J].

Guillena, Gabriela ;

Ramon, Diego J. ;

Yus, Miguel .

CHEMICAL REVIEWS, 2010, 110 (03) :1611-1641

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