Incorporation of 15N into Primary Amines via Isotopic Exchange DOI
Dirk Trauner, Michael D. Zott

Synfacts, Journal Year: 2023, Volume and Issue: 20(01), P. 0081 - 0081

Published: Dec. 8, 2023

Language: Английский

Photoinduced amination of iodoalkanes enabled by bifunctional O-benzoyl oxime DOI
Mengjie Zheng,

Xu-Kuan Qi,

Chao Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1949 - 1954

Published: Jan. 1, 2024

A photo-induced amination strategy that facilitates the transformation of iodoalkanes and bifunctional O -benzoyl oxime into alkyl amines is herein reported.

Language: Английский

Citations

1
Combining Umpolung and Carbon Isotope Exchange Strategies for Accessing Isotopically Labeled α-Keto Acids DOI

Jingran Ning,

Baoyang Du,

Shilong Cao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 5966 - 5971

Published: July 3, 2024

The integration of umpolung and carbon isotope exchange for accessing isotopically labeled α-keto acids through photoredox catalysis is elucidated. This process involves the carbonyl C(sp

Language: Английский

Citations

1
Modular Synthesis of Dehydroprolines by an Energy‐Transfer Enabled Cloke‐Wilson Rearrangement DOI
Austin D. Marchese, Tomislav Rovis

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Abstract A one‐pot photocatalytic method is reported for the generation of dehydroprolines, valuable precursors to 5‐aryl prolines. Imines, obtained via simple condensation aminocyclopropane carboxylates (ACPC) with a broad range aldehydes, were employed in this transformation without purification. We demonstrate energy‐transfer (EnT) enabled Cloke‐Wilson‐type rearrangement affords both rare 1,2‐dehydroprolines or more thermodynamically favored 1,5‐isomers up >20 : 1 selectivity directions, using an identical catalytic system from same starting material. Syntheses intermediates bioactive molecules high yields and highlight enabling transformation. Mechanistic studies support proposed triplet‐triplet EnT mode activation, distinct previously developed singlet excited states accessed UV excitation.

Language: Английский

Citations

1
Alkyl Triflimidate-Mediated Electrochemical Deaminative Functionalization DOI Creative Commons
Yi Wang,

Hui Shu,

Xiangzhang Tao

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 1, 2024

Abstract An efficient electrochemical strategy for the deaminative functionalization of alkyl amines has been described. The triflimidates was readily accessed by treatment primary with trifluoromethanesulfonic anhydride and unprecedentedly employed C − N bond activation. Under cellular conditions or promotion bases, can be applied to a range transformations, including boronation, sulfuration, selenization, sulfonation, oxidation, esterification, amidation.

Language: Английский

Citations

0
Molecular Editing of Toluene by Sequential meta-C–H/Benzylic C–N Deaminative Functionalizations DOI
Zhiwei Jiang,

Siquan He,

Yifei Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7431 - 7435

Published: Aug. 23, 2024

An approach to synthesizing structurally diverse toluene derivatives via sequential meta-C–H and benzylic C–N deaminative functionalization was developed by using a recyclable bifunctional directing template. The functionalized Katritzky salt intermediates are shown be engaged in wide range of carbon–carbon carbon–heteroatom bond formation reactions. synthetic utility the strategy demonstrated late-stage toloxatone.

Language: Английский

Citations

0
Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis DOI Creative Commons
Xiangzhang Tao, Wooseok Lee,

Zhimin Xu

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(47)

Published: Nov. 22, 2024

We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp 3 )–C(sp ) and 2 bonds from readily available alkyl bistriflimides. This methodology involves assembly two leaving groups on amines to form bistriflimides, followed by their effective coupling with wide range halides, pseudohalides, aryl alkenyl halides under electrochemical reductive conditions. Moreover, successful application relay transition metal–free cross-electrophile further demonstrates versatility bistriflimides as valuable building blocks in organic synthesis. Combined control experiments density functional theory calculations provide insights into reaction pathway crucial role iodide catalytic process.

Language: Английский

Citations

0
Modular Synthesis of Dehydroprolines by an Energy‐Transfer Enabled Cloke‐Wilson Rearrangement DOI
Austin D. Marchese, Tomislav Rovis

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Abstract A one‐pot photocatalytic method is reported for the generation of dehydroprolines, valuable precursors to 5‐aryl prolines. Imines, obtained via simple condensation aminocyclopropane carboxylates (ACPC) with a broad range aldehydes, were employed in this transformation without purification. We demonstrate energy‐transfer (EnT) enabled Cloke‐Wilson‐type rearrangement affords both rare 1,2‐dehydroprolines or more thermodynamically favored 1,5‐isomers up >20 : 1 selectivity directions, using an identical catalytic system from same starting material. Syntheses intermediates bioactive molecules high yields and highlight enabling transformation. Mechanistic studies support proposed triplet‐triplet EnT mode activation, distinct previously developed singlet excited states accessed UV excitation.

Language: Английский

Citations

0
Alkyl Bistriflimidate-Mediated Electrochemical Deaminative Functionalization DOI Creative Commons
Hui Shu, Xiangzhang Tao, Shengyang Ni

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

The readily available alkyl triflimidate reagent NTf2 has been used for deaminative C–B, C–S, C–Se, and C–Te bond formations. This protocol could be applied to a variety of transformations, demonstrating its potential primary amine functionlization.

Language: Английский

Citations

0
Synthesis of 15N-Pyridines and Higher Mass Isotopologs via Zincke Imine Intermediates DOI Creative Commons
Hillary M. H. Nguyen, D. Thomas, Marie A. Hart

et al.

Published: Nov. 2, 2023

Methods to incorporate stable radioisotopes are integral pharmaceutical and agrochemical development. However, despite the prevalence of pyridines in candidate compounds, methods 15N-atoms within their structures limited. Here, we present a general approach pyridine 15N-labeling that proceeds via ring-opening NTf-Zincke imines then ring-closure with commercially available 15NH4Cl salts. This process functions on range substituted pyridines, from simple building block-type compounds late-stage labeling complex pharmaceuticals, 15N-incorporation is >95% most cases. The reactivity Zincke imine intermediates also enables deuteration C3- C5-positions, resulting higher mass isotopologs required for LCMS analysis biological fluids during drug

Language: Английский

Citations

0
Incorporation of 15N into Primary Amines via Isotopic Exchange DOI
Dirk Trauner, Michael D. Zott

Synfacts, Journal Year: 2023, Volume and Issue: 20(01), P. 0081 - 0081

Published: Dec. 8, 2023

Language: Английский

Citations

0