Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 27, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202201883
Keywords
Alkynes; Boron; Borylstannylation; Radical Reactions; Tin
Categories
Funding
- JST CREST, Japan [JPMJCR20R3]
- Ministry of Education, Culture, Sports, Science & Technology, Japan [21H05212]
- JSPS KAKENHI [JP19K05455]
- Grants-in-Aid for Scientific Research [21H05212] Funding Source: KAKEN
Ask authors/readers for more resources
We have achieved the first anti-borylstannylation of alkynes by using (o-phenylenediaminato)borylstannanes. This reaction provides 1-boryl-2-stannylalkenes with excellent regio- and stereoselectivity through a radical mechanism. The mild reaction conditions allow for a wide range of substrates, and the products can be further used in cross- or homocoupling reactions to synthesize important compounds.
We have achieved the first anti-borylstannylation of alkynes by using (o-phenylenediaminato)borylstannanes. This reaction afforded 1-boryl-2-stannylalkenes with excellent regio- and stereoselectivity by a radical mechanism. This anti-addition manner is in sharp contrast to the syn-selectivity obtained during transition metal-catalyzed borylstannylation. The mild radical conditions enabled a broad substrate scope, and various types of aromatic and aliphatic alkynes were applicable. The origin of regio- and stereoselectivity was elucidated by DFT calculation of the reaction mechanism. The application of the borylstannylation products to cross- or homocoupling reactions provided ready access to either triarylethenes or bisborylbutadienes.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available