Citation: Jiahang Lv, Binlin Zhao, Ying Han, Yu Yuan, Zhuangzhi Shi. Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds[J]. Chinese Chemical Letters, ;2021, 32(2): 691-694. doi: 10.1016/j.cclet.2020.06.028 shu

Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds

Jiahang Lv ^{a, b, 1} ,
Binlin Zhao ^{c, 1} ,
Ying Han ^{a, *,} ,
Yu Yuan ^a ,
Zhuangzhi Shi ^{a, b, *,}

a.
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
b.
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
c.
Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China

hanying@yzu.edu.cn

shiz@nju.edu.cn

Received Date: 22 May 2020
Revised Date: 8 June 2020
Accepted Date: 19 June 2020
Available Online: 23 June 2020

Figures(5)

Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C−C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient example of catalyst- and metal-free aminoboration of alkynes and C−C bond formation with diazo compounds to produce C3-substituted indoles. Diverse alkynylanilines and diazo compounds can be utilized for this tandem transformation under mild reaction conditions, resulting in broad functional group compatibility. Additionally, this metal-free strategy can be extended to construct substituted benzofurans.
- Indoles,
- Aminoboration,
- Metal-free,
- BCl₃,
- Diazo compounds
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