One-Pot Synthesis of Imines and Secondary Amines by Pd-Catalyzed Coupling of Benzyl Alcohols and Primary Amines

被引：193

作者：

Kwon, Min Serk ^{[2
]}

Kim, Sungjin ^{[1
]}

Park, Sungho ^{[1
]}

Bosco, William ^{[1
]}

Chidrala, Ravi Kumar ^{[1
]}

Park, Jaiwook ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 790784, Kyeongbuk, South Korea

[2] POSCO, Tech Res Labs, Elect Steel Res Grp, Pohang 790300, Kyeongbuk, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 07期

关键词：

BAYLIS-HILLMAN REACTION; ACID-DERIVATIVES; HYDROGENATION; ALKYLATION; REDUCTION; OXIDATION; ALDEHYDES; VERSATILE; INDOLES; KETONES;

D O I：

10.1021/jo8026609

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imines and secondary amines were synthesized selectively by controlling reaction conditions for the Pd-catalyzed one-pot reactions of benzyl alcohols with primary amines. The reactions did not require any additives and were effective for a wide range of alcohols and amines.

引用

页码：2877 / 2879

页数：3

共 38 条

[1] A novel synthesis of disubstituted ureas using titanium(IV) isopropoxide and sodium borohydride [J].

Armstrong, JD ;

Wolfe, CN ;

Keller, JL ;

Lynch, J ;

Bhupathy, M ;

Volante, RP ;

DeVita, RJ .

TETRAHEDRON LETTERS, 1997, 38 (09) :1531-1532

[2] Selective formation of α-methylene-β-amino acid derivatives through the aza version of the Baylis-Hillman reaction [J].

Balan, D ;

Adolfsson, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6498-6501

[3] Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling [J].

Balraju, V. ;

Iqbal, Javed .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8954-8956

[4] REDUCTION OF SCHIFF BASES .2. BENZHYDRYLAMINES AND STRUCTURALLY RELATED COMPOUNDS [J].

BILLMAN, JH ;

TAI, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (04) :535-539

[5] In situ oxidation-imine formation-reduction routes from alcohols to amines [J].

Blackburn, L ;

Taylor, RJK .

ORGANIC LETTERS, 2001, 3 (11) :1637-1639

[6] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[7] STUDIES ON THE PREPARATION AND REACTIONS OF TRITYLSULFENIMINES [J].

BRANCHAUD, BP .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3531-3538

[8] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

[9] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[10] LIQUID CRYSTALS .2. EFFECTS OF TERMINAL GROUP SUBSTITUTION ON MESOMORPHIC BEHAVIOR OF SOME BENZYLIDENEANILINES [J].

CASTELLANO, JA ;

GOLDMACHER, JE ;

BARTON, LA ;

KANE, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (09) :3501-+

← 1 2 3 4 →