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1.
Beilstein J Org Chem ; 20: 205-211, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38318457

RESUMO

A convenient and efficient method for the synthesis of optically active difluoro-substituted indoline derivatives starting from the corresponding 3H-indoles by chiral phosphoric acid-catalyzed transfer hydrogenation was developed. Using Hantzsch ester as the hydrogen source under mild reaction conditions, the target products can be obtained with excellent yield and enantioselectivity.

2.
Angew Chem Int Ed Engl ; 58(24): 8187-8191, 2019 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-30990948

RESUMO

The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C-B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII /IrV cycle.

3.
Org Lett ; 25(16): 2878-2882, 2023 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-37057845

RESUMO

A metal-free protocol for visible-light-driven intramolecular hydrodifluoroacetylative cyclization of N-propargyl or N-homopropargyl-2-bromo-2,2-difluoroacetamide to α,α-difluorinated ß-substituted γ- or δ-lactam without an additional photosensitizer has been developed. By using thiol and Hantzsch ester as the catalyst and hydrogen donor, respectively, to implement a hydrogen atom transfer process, moderate to high (Z) selectivity was achieved. The results of a mechanistic investigation revealed the critical contribution of the thiol catalyst in attaining the stereoselectivity.

4.
Chem Commun (Camb) ; 58(8): 1135-1138, 2022 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-34981092

RESUMO

A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent could tackle the deleterious effect of the coordinative cyanide ion in the asymmetric alkene arylcyanation.

5.
Org Lett ; 23(7): 2527-2532, 2021 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-33760622

RESUMO

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

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