Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 17, 2024

Abstract 1,2‐Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N‐functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2‐diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N ‐heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2‐aminothiolation styrenes.

Язык: Английский

Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover DOI Open Access
Pierre Palamini, Alexandre A. Schoepfer, Jérôme Waser

и другие.

Angewandte Chemie, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Abstract The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical‐polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2‐azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Язык: Английский

Процитировано

0
Stereospecific Aminative Cyclizations Triggered by Intermolecular Aza‐Prilezhaev Alkene Aziridination DOI Creative Commons
Matthew J. S. Smith,

Wenbin Tu,

Craig M. Robertson

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(48)

Опубликована: Окт. 17, 2023

Under acidic reaction conditions (TFA), deprotection of BocNR(OSO2 R) reagents triggers intermolecular aminative cyclizations alkenes equipped with pendant nucleophiles. The processes are predicated on a sequence stereospecific aza-Prilezhaev aziridination followed by SN 2-like opening the nucleophile. method offers broad scope respect to nucleophile (N-, O- or C-based), alkene and cyclization mode, allowing installation two contiguous stereocenters under operationally simple conditions.

Язык: Английский

Процитировано

7
Trifluoromethylarylation of alkenes using anilines DOI Creative Commons
Carlos Corral Suarez, Ignacio Colomer

Chemical Science, Год журнала: 2023, Номер 14(43), С. 12083 - 12090

Опубликована: Янв. 1, 2023

Nitrogen containing compounds, such as anilines, are some of the most widespread and useful chemical species, although their high unselective reactivity has prevented incorporation into many interesting transformations, functionalization alkenes. Herein we report a method that allows trifluoromethylarylation alkenes using for first time, with no need additives, transition metals, photocatalysts or an excess reagents. An in-depth mechanistic study reveals key role hexafluoroisopropanol (HFIP) unique solvent, establishing hydrogen bonding network aniline trifluoromethyl reagent, is responsible altered exquisite selectivity. This work uncovers new mode involves use abundant anilines non-prefunctionalized aromatic source simultaneous activation hypervalent iodine reagent.

Язык: Английский

Процитировано

7
A Scalable and Metal-Free Synthesis of Indazoles from 2-Aminophenones and In Situ Generated De-Boc-Protected O-Mesitylsulfonyl Hydroxylamine Derivatives DOI
Jinlong Wang, Dongmin Shi, Zihao Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13049 - 13056

Опубликована: Авг. 30, 2023

A one-pot metal-free protocol to access indazoles from easily available 2-aminophenones and hydroxylamine derivatives has been achieved. The reaction is operationally simple, mild, insensitive air moisture. broad range of were prepared in good excellent yield (up 97% yield), the displayed a functional group tolerance. was performed at gram scale, its synthetic application exhibited through rapid efficient preparation bioactive molecule YC-3 FDA-approved drug axitinib.

Язык: Английский

Процитировано

6
Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 17, 2024

1,2-Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N-functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2-diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N-heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2-aminothiolation styrenes.

Язык: Английский

Процитировано

2
A Povarov-Type Reaction to Access Tetrahydroquinolines from N-Benzylhydroxylamines and Alkenes in HFIP DOI Creative Commons
Valentyn Pozhydaiev,

Daniella Al-Othman,

Joseph Moran

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(76), С. 10504 - 10507

Опубликована: Янв. 1, 2024

Here, we report the synthesis of tetrahydroquinolines between newly developed

Язык: Английский

Процитировано

2
I2-Mediated [6 + 1] Annulation of Alkynes with MsONH3OTf: Direct Synthesis of Benzo[b]azepines DOI

Daijiao Zhuang,

Shixuan Jiang,

Youzhi Wang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(17), С. 3007 - 3012

Опубликована: Апрель 21, 2023

The synthesis of benzo[b]azepines using protonated aminating reagent (MsONH3OTf) and alkynes through I2-mediated [6 + 1] annulation reaction has been developed. This protocol features excellent functional group tolerance mild conditions affords the in moderate to good yields under metal-free conditions.

Язык: Английский

Процитировано

5
Recent Advances in Nonprecious Metal Catalysis DOI
David J. Bernhardson, Eric C. Hansen, Aran K. Hubbell

и другие.

Organic Process Research & Development, Год журнала: 2023, Номер 27(11), С. 1913 - 1930

Опубликована: Сен. 13, 2023

As the field of nonprecious metal catalysis continues to expand, we pursue a review series covering selected transformations in this area over short time interval highlight advancements. We seek raise awareness both current art and need continue development toward broader application or earth-abundant metals chemical pharmaceutical industries.

Язык: Английский

Процитировано

5
Synthesis of 1-Aryltetralins via Re2O7/HReO4 Mediated Intramolecular Hydroarylations DOI

Rukhsar Gul,

Liqun Hu,

Yibing Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 12079 - 12086

Опубликована: Авг. 10, 2023

Here, we describe highly efficient intramolecular hydroarylations mediated by Re2O7/HReO4. Styrene derivatives of different electronic properties have been activated to effect a challenging hydroarylation for the facile access various substituted 1-aryltetralin structures. This method is characterized mild reaction conditions, broad substrate scope, high chemical yields, and 100% atom economy. The potential synthetic application this methodology was exemplified total synthesis an isoCA-4 analogue.

Язык: Английский

Процитировано

2
Catalytic Synthesis of β‐(Hetero)arylethylamines: Modern Strategies and Advances DOI Creative Commons
Valentyn Pozhydaiev, Cyprien Muller, Joseph Moran

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(41)

Опубликована: Авг. 21, 2023

Abstract β‐(Hetero)arylethylamines appear in a myriad of pharmaceuticals due to their broad spectrum biological properties, making them prime candidates for drug discovery. Conventional methods preparation often require engineered substrates that limit the flexibility synthetic routes and diversity compounds can be accessed. Consequently, provide rapid versatile access those scaffolds remain limited. To overcome these challenges, chemists have designed innovative modular strategies β‐(hetero)arylethylamine motif, paving way more extensive use future pharmaceuticals. This review outlines recent progresses synthesis (hetero)arylethylamines emphasizes how innovations enabled new levels molecular complexity, selectivity, practicality.

Язык: Английский

Процитировано

1