The synthesis of alkenylated-o-carboranes via photoalkenylation of iodocarboranes with unactivated alkenes has been achieved. This strategy features a transition metal-free protocol, a light-promoted reaction under mild reaction conditions, broad substrate scope and good functional group tolerance. Control experiments suggest that the reaction may involve the cage C-centered radical species.

Scope (computer science)

Functional group

Reaction conditions

10.1039/d1dt03726a

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Citations (8)

Rhodium‐Catalyzed Cascade Reactions of Indoles with 4‐Hydroxy‐2‐Alkynoates for the Synthesis of Indole‐Fused Polyheterocycles

Advanced Synthesis & Catalysis (2020)

Xiaowei Wu Pinyi Li Yangbin Lu Qiao Jin Jingwei Zhao

Abstract Herein, an efficient and regioselective Rh(III)‐catalyzed [4+2] annulation/lactonization cascade of indoles with 4‐hydroxy‐2‐alkynoates at room temperature to access the furo[3′,4′:4,5]pyrimido[1,6‐ a ]indole‐1,5(3 H ,4 H )‐diones is described. This method features mild reaction conditions, operational simplicity, excellent regioselectivity, broad substrate scope with good functional group tolerance, and good to excellent yields. magnified image

Annulation

Reaction conditions

Functional group

10.1002/adsc.202000493

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Citations (35)

CCDC 1984364: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Xiuwen Jia Pinyi Li Xiaoning Zhang Siyu Liu Xingzi Shi

10.5517/ccdc.csd.cc24lwrd

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Visible-Light-Promoted Fe(III)-Catalyzed N–H Alkylation of Amides and N-Heterocycles

The Journal of Organic Chemistry (2022)

Hangcheng Ni Chaoming Li Xingzi Shi Xianyue Hu Hui Mao

The combination of the radical chemistry of ligand-to-metal charge transfer with metal catalysis by a single iron salt helps to realize the visible-light-promoted N-H alkylation of amides and N-heterocycles. A wide variety of amides and nitrogen-containing heterocycles were tolerated in our protocol to give N-alkylated products. The applicability of this protocol was further demonstrated by late-stage alkylation of N-H-containing pharmaceuticals. Moreover, N-H-alkylated α-amino tetrahydrofurans could be transformed into versatile ring-opened amino alcohols under reducing conditions. A mechanistic study revealed that hydrogen atom transfer by a tert-butoxyl radical and a chlorine radical was responsible for the activation of C(sp3)-H precursors.

Photoredox catalysis

Hydrogen atom

10.1021/acs.joc.2c00854

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Citations (20)

Light-promoted borylation and lactonization of propargyl acetates using NHC-borane

RSC Advances (2025)

Hangcheng Ni Li Yu Chaoming Li Zhenxiang Liu

In the absence of photoredox catalyst, we achieved radical borylation and lactonization of propargyl acetates under light irradiation using N-heterocyclic carbene borane, leading to the synthesis of substituted 4-(NHC-boryl)-2(5 H )-furanones.

Borylation

Propargyl

Boranes

10.1039/d4ra08656b

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Frontispiz: Photoarylation of Iodocarboranes with Unactivated (Hetero)Arenes: Facile Synthesis of 1,2‐[(Hetero)Aryl]_n‐o‐Carboranes (n=1,2) and o‐Carborane‐Fused Cyclics

Angewandte Chemie (2017)

Hangcheng Ni Zaozao Qiu Zuowei Xie

>Carborane: In der Zuschrift auf S. 730 beschreiben Z. Xie und Mitarbeiter die übergangsmetallfreie Photoarylierung von Iodcarboranen mit nichtaktivierten (Hetero)Arenen. Eine Vielzahl von (hetero)arylierten o-Carboranen ist damit zugänglich.

Carborane

10.1002/ange.201780361

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CCDC 1983959: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Xiaowei Wu Pinyi Li Yangbin Lu Qiao Jin Jingwei Zhao

10.5517/ccdc.csd.cc24lgpx

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Photoarylation of Iodocarboranes with Unactivated (Hetero)Arenes: Facile Synthesis of 1,2‐[(Hetero)Aryl]_n‐o‐Carboranes (n=1,2) and o‐Carborane‐Fused Cyclics

Angewandte Chemie International Edition (2016)

Hangcheng Ni Zaozao Qiu Zuowei Xie

Abstract Photoarylation of iodocarboranes with unactivated arenes/heteroarenes at room temperature has been achieved, for the first time, thus leading to the facile synthesis of a large variety of cage carbon mono(hetero)arylated and di(hetero)arylated o‐carboranes. This work represents a clean, efficient, transition‐metal‐free, and cheap synthesis of functionalized carboranes, which has significant advantages over the known methods.

Carbon fibers

10.1002/anie.201610810

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Citations (38)

CCDC 2079908: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Fei Zhao Qiao Jin Yangbin Lu Xiaoning Zhang Long Dai

10.5517/ccdc.csd.cc27t9t6

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