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1.
Org Lett ; 22(16): 6543-6546, 2020 08 21.
Article in English | MEDLINE | ID: mdl-32806139

ABSTRACT

An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.

2.
Org Lett ; 19(1): 194-197, 2017 01 06.
Article in English | MEDLINE | ID: mdl-27997200

ABSTRACT

The impact of varying percentages of an organic solvent added to reactions run in aqueous nanomicelles as the reaction medium has been investigated. Issues such as rates of reaction, percent conversion, and yield, as well as various practical aspects (e.g., effect on stirring, etc.), are discussed, leading to an operationally simple method for the general improvement of potentially problematic systems across a broad range of reaction types, in particular for reactions run at scale.

3.
Org Lett ; 17(16): 3968-71, 2015 Aug 21.
Article in English | MEDLINE | ID: mdl-26251952

ABSTRACT

A general and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium is described. Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M represents mild conditions associated with these valuable types of couplings. The aqueous reaction medium is recyclable leading to low E Factors.


Subject(s)
Amides/chemical synthesis , Peptides/chemical synthesis , Water/chemistry , Amides/chemistry , Imines/chemistry , Indicators and Reagents , Molecular Structure , Morpholines/chemistry , Peptides/chemistry , Pyridines/chemistry , Surface-Active Agents/chemistry , Temperature
4.
Angew Chem Int Ed Engl ; 53(51): 14051-4, 2014 Dec 15.
Article in English | MEDLINE | ID: mdl-25323663

ABSTRACT

The addition of NaBH4 to Pd(OAc)2 in water containing nanomicelles leads to the generation of H2 and Pd nanoparticles. Subsequent reduction of disubstituted alkynes affords Z-alkenes in high yields. These reactions are general, take place in water at ambient temperatures, and offer recycling of the aqueous reaction mixture along with low overall E Factors.


Subject(s)
Alkynes/chemistry , Metal Nanoparticles/chemistry , Palladium/chemistry , Temperature , Water/chemistry , Hydrogenation , Micelles , Molecular Structure , Stereoisomerism
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