Hafnium Trifluoromethanesulfonate (Hafnium Triflate) as a Highly Efficient Catalyst for Chemoselective Thioacetalization and Transthioacetalization of Carbonyl Compounds
2008
Abstract
A range of carbonyl compds. including aliph. and arom. aldehydes and ketones were converted to the corresponding thioacetals in high yields in the presence of a catalytic amt. of hafnium trifluoromethanesulfonate (0.1 mol%, room temp.). The mild conditions tolerated various sensitive functional and protecting groups and were racemization-free when applied to alpha -aminoaldehydes. Transacetalization and chemoselective thioacetalization of arom. aldehydes in the presence of aliph. aldehydes and ketones were also documented. [on SciFinder (R)]
Details
Title
Hafnium Trifluoromethanesulfonate (Hafnium Triflate) as a Highly Efficient Catalyst for Chemoselective Thioacetalization and Transthioacetalization of Carbonyl Compounds
Author(s)
Wu, Yan-Chao ; Zhu, Jieping
Published in
Journal of Organic Chemistry
Volume
73
Issue
23
Pages
9522-9524
Date
2008
ISSN
0022-3263
Keywords
Carbonyl compounds Role: PRP (Properties); RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); Acetalization (thioacetalization; hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); hafnium trifluoromethanesulfonate catalyst chemoselective thioacetalization transthioacetalization carbonyl compd
Note
CAN 149:513411
22-4
Physical Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
7334-55-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (hafnium trifluoromethanesulfonate as catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 161337-67-3 (Hafnium trifluoromethanesulfonate) Role: CAT (Catalyst use), USES (Uses) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 1073536-45-4P; 1073536-46-5P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 5425-44-5P; 5616-55-7P; 6302-92-7P; 7334-52-3P; 7695-69-4P; 22914-06-3P; 23837-15-2P; 60340-45-6P; 66605-57-0P; 69895-02-9P; 108164-52-9P; 114478-85-2P; 114478-87-4P; 134836-75-2P; 141620-70-4P; 352652-96-1P; 496045-97-7P; 609368-30-1P; 854022-23-4P; 1073536-40-9P; 1073536-41-0P; 1073536-42-1P; 1073536-43-2P; 1073536-47-6P; 1073536-48-7P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 66-99-9 (2-Naphthalenecarboxaldehyde); 75-08-1 (Mercaptoethane); 98-86-2; 100-10-7; 100-52-7 (Benzaldehyde); 101-48-4 (2,2-Dimethoxyethylbenzene); 104-88-1; 105-07-7; 108-98-5 (Mercaptobenzene); 109-80-8 (1,3-Dimercaptopropane); 122-78-1 (Benzeneacetaldehyde); 123-08-0; 123-11-5; 540-63-6 (1,2-Dimercaptoethane); 555-16-8; 613-45-6; 830-79-5; 1122-91-4; 1125-88-8 (Dimethoxymethylbenzene); 2103-57-3; 2550-26-7; 3132-99-8; 6630-33-7; 60656-87-3; 69404-94-0; 72155-45-4; 854022-39-2; 1073536-50-1 Role: RCT (Reactant), RACT (Reactant or reagent) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.)
22-4
Physical Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
7334-55-6P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (hafnium trifluoromethanesulfonate as catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 161337-67-3 (Hafnium trifluoromethanesulfonate) Role: CAT (Catalyst use), USES (Uses) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 1073536-45-4P; 1073536-46-5P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 5425-44-5P; 5616-55-7P; 6302-92-7P; 7334-52-3P; 7695-69-4P; 22914-06-3P; 23837-15-2P; 60340-45-6P; 66605-57-0P; 69895-02-9P; 108164-52-9P; 114478-85-2P; 114478-87-4P; 134836-75-2P; 141620-70-4P; 352652-96-1P; 496045-97-7P; 609368-30-1P; 854022-23-4P; 1073536-40-9P; 1073536-41-0P; 1073536-42-1P; 1073536-43-2P; 1073536-47-6P; 1073536-48-7P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.); 66-99-9 (2-Naphthalenecarboxaldehyde); 75-08-1 (Mercaptoethane); 98-86-2; 100-10-7; 100-52-7 (Benzaldehyde); 101-48-4 (2,2-Dimethoxyethylbenzene); 104-88-1; 105-07-7; 108-98-5 (Mercaptobenzene); 109-80-8 (1,3-Dimercaptopropane); 122-78-1 (Benzeneacetaldehyde); 123-08-0; 123-11-5; 540-63-6 (1,2-Dimercaptoethane); 555-16-8; 613-45-6; 830-79-5; 1122-91-4; 1125-88-8 (Dimethoxymethylbenzene); 2103-57-3; 2550-26-7; 3132-99-8; 6630-33-7; 60656-87-3; 69404-94-0; 72155-45-4; 854022-39-2; 1073536-50-1 Role: RCT (Reactant), RACT (Reactant or reagent) (hafnium trifluoromethanesulfonate hafnium triflate as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compds.)
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2010-11-25