One-step Multi-functionalization of Aromatic Alkynes

Aromatic alkyne allows efficient ortho di-functionalization of the aromatic ring. For example, the aryne precursor Kobayashi can functionalize two groups at the 1,2-position of the benzene ring. Would it be possible to achieve tri-functionalization of aromatic rings by aromatic alkynes?

Dr. Yang Li has developed a novel domino aryne precursor 2-(Trimethylsilyl)-1,3-phenylene bis(trifluoromethanesulfonate) 
(TPBP), which can functionalize three different groups at the 1,2,3-position of the benzene ring through a sequential domino process. 

TPBT can be activated by F- or CO32- under mild conditions to release domino aromatic alkyne intermediates (Fig. 1). TPBT can interact with different nucleophilic and electrophilic reagents to obtain various 1,2,3-trisubstituted benzene derivatives, and can also prepare 1,3- and 1,2-dinucleophilic products.

Fig.1 TPBT and its aromatic alkyne intermediate



  • Adaptable to a wide range of reaction types, with mild reaction conditions and broad functional group compatibility
  • Able to achieve tri-functionalization of the benzene ring



Fig.2 The reaction of TPBT and sulfonamides can obtain different products simply by varying the reaction conditions



Qiu, Dachuan, Jia He, Xiao Yue, Jiarong Shi, and Yang Li. "Diamination of Domino Aryne Precursor with Sulfonamides." Organic letters 18, no. 13 (2016): 3130-3133.



    TPBT, 95%
    CAS: 1639418-72-6

    Synthetic Reagents

    432915 Triethylamine, 99% (CAS: 121-44-8)
    909000 Lithium trifluoromethanesulfonate, 99.5% (CAS: 33454-82-9)
    252705 Trifluoroacetic acid, 99% (CAS: 76-05-1)

    Dr. Li’s Profile

    He is a professor from Chongqing University. One of his main research interests is synthetic organic chemistry, i.e., to construct molecular skeletons efficiently and precisely through green chemistry, and provide new strategies for the synthesis of biologically and pharmaceutically active molecules.

    By QiChuck


    Just added to your wishlist:
    My Wishlist
    You've just added this product to the cart:
    Go to cart page