Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide

被引:68
作者
Banerjee, M [1 ]
Roy, S [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Organomet & Catalysis Lab, Kharagpur 721302, W Bengal, India
关键词
D O I
10.1021/ol0493352
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A reagent combination of beta-SnO and catalytic [Rh(COD)CI](2) in THF-H2O promotes the reaction of propargyl bromides and aldehydes and directs the regioselectivity toward the formation of either allenic alcohols or homopropargylic alcohols. This highly regioselective either/or transformation proceeds via a transmetalation from rhodium to tin, in which metallotropic rearrangement between a propargylmetal and allenylmetal is arrested.
引用
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页码:2137 / 2140
页数:4
相关论文
共 20 条
[1]   Palladium(0) catalyzed regioselective carbonyl propargylation across tetragonal tin(II) oxide via redox transmetallation [J].
Banerjee, M ;
Roy, S .
CHEMICAL COMMUNICATIONS, 2003, (04) :534-535
[2]   SYNTHESIS, REACTIONS AND CATALYTIC ACTIVITIES OF SIGMA AND ETA-3-ALLYL-BIS(TRIPHENYLSTIBINE)RHODIUM(III) COMPLEXES [J].
CHIN, CS ;
SHIN, SY ;
LEE, CG .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (07) :1323-1326
[3]   A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS [J].
COREY, EJ ;
YU, CM ;
LEE, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :878-879
[4]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P3590
[5]   Remarkable electronic effect on rhodium-catalyzed carbonyl additions and conjugated additions with arylmetallic reagents [J].
Huang, TS ;
Meng, Y ;
Venkatraman, S ;
Wang, D ;
Li, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7451-7452
[6]   Reactions of Rh(SbPh3)3(CO)X (X = Cl, Pr) with organic propargyl compounds.: Synthesis, structure and reactivity of rhodiacyclopent-3-ene-2-one complexes [J].
Kayan, A ;
Gallucci, JC ;
Wojcicki, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 630 (01) :44-56
[7]   An unusual reaction of Rh(SbPh3)3(CO)Cl with propargyl halides:: the formation of rhodiacyclopent-3-ene-2-one complexes [J].
Kayan, A ;
Gallucci, JC ;
Wojcicki, A .
INORGANIC CHEMISTRY COMMUNICATIONS, 1998, 1 (11) :446-448
[8]   Oxidative addition reactions of Rh(SbPh3)3(CO)X (X = Cl, Br) with organic phenyl-substituted propargyl compounds.: Rhodium(III) phenylpropargyl products and their conversion to rhodiacyclic complexes [J].
Kayan, A ;
Wojcicki, A .
INORGANICA CHIMICA ACTA, 2001, 319 (1-2) :187-193
[9]   Grignard-type carbonyl phenylation in water and under an air atmosphere [J].
Li, CJ ;
Meng, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9538-9539
[10]   Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the α-carbon atom [J].
Ma, SM .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (09) :701-712