Direct Conversion of Alcohols to Acetals and H2 Catalyzed by an Acridine-Based Ruthenium Pincer Complex

被引：229

作者：

Gunanathan, Chidambaram ^{[1
]}

Shimon, Linda J. W. ^{[2
]}

Milstein, David ^{[1
]}

机构：

[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel

[2] Weizmann Inst Sci, Unit Chem Res Support, IL-76100 Rehovot, Israel

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 09期

关键词：

ALDEHYDES; ESTERS; OXIDATION; EFFICIENT;

D O I：

10.1021/ja808893g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The crystallographically characterized ruthenium complex RuHCl(A-'Pr-PNP)(CO) (1) [A-'Pr-PNP = 4,5-bis-(diisopropylphosphinomethyl)acridine], which bears a nonplanar acridine moiety, catalyzes in a neutral medium the transformation of primary alcohols to the corresponding acetals with the liberation of H-2. In the presence of base, complex I catalyzes the dehydrogenative coupling of alcohols to form esters. Acetal formation may involve hemiacetal dehydration to form an enol ether followed by alcohol addition to the double bond.

引用

页码：3146 / +

页数：3

共 19 条

[1] Concerning the stability of benzyl alcohol: formation of benzaldehyde dibenzyl acetal under aerobic conditions [J].

Abend, AM ;

Chung, L ;

Bibart, RT ;

Brooks, M ;

McCollum, DG .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2004, 34 (05) :957-962

[2]

BERGSTROM RG, 1980, CHEM ETHERS CRO 2 SE, pCH20

[3] CHEMISTRY OF ENOL ETHERS [J].

EFFENBER.F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (05) :295-&

[4] Solvent-free oxidation of primary alcohols to aldehydes using Au-Pd/TiO2 catalysts [J].

Enache, DI ;

Edwards, JK ;

Landon, P ;

Solsona-Espriu, B ;

Carley, AF ;

Herzing, AA ;

Watanabe, M ;

Kiely, CJ ;

Knight, DW ;

Hutchings, GJ .

SCIENCE, 2006, 311 (5759) :362-365

[5]

*FEMA, 4370 FEMA

[6] Selective Synthesis of Primary Amines Directly from Alcohols and Ammonia [J].

Gunanathan, Chidambaram ;

Milstein, David .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8661-8664

[7] An efficient and versatile procedure for the synthesis of acetals from aldehydes and ketones catalyzed by lithium tetrafluoroborate [J].

Hamada, N ;

Kazahaya, K ;

Shimizu, H ;

Sato, T .

SYNLETT, 2004, (06) :1074-1076

[8] 4,5-bis(diphenylphosphino)acridine:: A new type of tridentate phosphorus-nitrogen-phosphorus ligands [J].

Hillebrand, S ;

Bartkowska, B ;

Bruckmann, J ;

Krüger, C ;

Haenel, MW .

TETRAHEDRON LETTERS, 1998, 39 (08) :813-816

[9] SELECTIVE DIMERIZATION OF ALDEHYDES TO ESTERS CATALYZED BY HYDRIDORUTHENIUM COMPLEXES [J].

ITO, T ;

HORINO, H ;

KOSHIRO, Y ;

YAMAMOTO, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (02) :504-512

[10] A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate [J].

Leonard, NM ;

Oswald, MC ;

Freiberg, DA ;

Nattier, BA ;

Smith, RC ;

Mohan, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5202-5207

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