scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Zhanghua Gao

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

2022 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Jia Chen ◽  
...  

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.


2021 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Zhanghua Gao

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.


2021 ◽  
Author(s):  
Zhiqiang Liu ◽  
Goutam Kumar Kole ◽  
Yudha P. Budiman ◽  
Ya-Ming Tian ◽  
Alexandra Friedrich ◽  
...  

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Mitsuhiro Ueda ◽  
Kota Nishimura ◽  
Ryo Kashima ◽  
Ilhyong Ryu

2016 ◽  
Vol 11 (7) ◽  
pp. 1934578X1601100
Author(s):  
Takuya Tashiro ◽  
Shinobu Honzawa ◽  
Takumichi Sugihara

Piceatannol (3,3′,4,5′-tetrahydroxy- trans-stilbene, 2), an oxygenated analog of resveratrol (1), was synthesized. It is one of the naturally occurring polyphenolic stilbenoids contained in red wine, and possesses many kinds of beneficial effects such as anticancer activity. The trans-stilbene skeleton of 2 was constructed by Pd-catalyzed Suzuki-Miyaura cross coupling reaction of triflate 8 with ( E)-alkenylboronoate 13. The key intermediate 13 was prepared diastereoselectively by acid-catalyzed hydroboration of pinacolborane 12 to alkyne 11.


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