HOME The Chuang Research Group

We work on development of new synthetic methodology with focus on  phosphine-mediated reaction and transition-metal catalyzed C-H bond activation. The developed methodology can be further demonstrated toward synthesis of novel fullerene C60/C70 derivatives for application in the organic solar cells.

       Research gate       

Our research program:

1. Educate and mentor students

2. Broaden students' scientific viewpoints

3. Lead students to uncover questions and solve significant questions by scientific approaches


A Frontipiece published in Adv. Funct. Mater.201525, 207.


Recently published:

Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

 Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan
 Department of Chemistry, National Tsing Hua University, Hsinchu 30010, Taiwan
§ Instrumentation Center, National Taiwan University, Taipei 10617, Taiwan
Org. Lett.201921 (4), pp 1182–1186.

Abstract

Abstract Image

A palladium-catalyzed C–H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C–H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C–H bond functionalizations. Additionally, nondirected C–H bond functionalization at the C-4′ position with alkenes rendered complete C–H functionalization of five C–H bonds that formed a stable hexasubstituted benzene ring.


Communication

Palladium‐Catalyzed Benzofulvenation of o‐Arylanilines through C−H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene

Adv. Synth. Catal. 2019, 361, 683-689.

Abstract

We report the first example of Pd(II)‐catalyzed highly step‐ and atom‐economical benzofulvenation through free amine‐directed ortho C−H bond activation of o‐arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o‐arylaniline substrates through C−H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics.

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Research topics:

1. Conjugate alpha-addition reaction


Deng, J.-C.; Kuo, C.-W.; Chuang, S.-C.* Chem. Commun., 2014, 50, 1058010583.


2. Transition-metal-catalyzed C-H bond activation

Rajeshkumar, V.; Lee, T.-H.; Chuang, S.-C.* Org. Lett. 2013, 15, 14681471.


3. Organic photovoltaics

Chen, C.-P.*; Huang, C.-Y.; Chuang, S.-C.* Adv. Funct. Mater., 2015, 25, 207213.


4. Fullerene C60/C70 chemistry

Tseng, B.-Y.; Chuang, S.-C.* Adv. Synth. & Catal. 2013, 355, 21652171.