We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Mechanism of Borane‐Catalyzed Oligomerization of Arylallenes and Arylacetylenes.
- Authors
Qu, Zheng‐Wang; Zhu, Hui; Grimme, Stefan
- Abstract
Recently, it was shown that Piers' borane [HB(C6F5)2]2 can induce rapid oligomerization reactions of arylacetylenes and arylallenes. Using phenylallene PhCH=C=CH2 and phenylacetylene PhCCH as typical substrates, the detailed mechanisms of borane‐induced oligomerization are disclosed by extensive state‐of‐the‐art DFT calculations. Following initial regioselective hydroboration of unsaturated C=C or C≡C bonds, further oligomerization and structural rearrangement reactions may occur through unique boryl‐enabled conversions such as 1,3‐boryl‐shift, allylboration, 1,2‐carboboration, and 1,5‐electrocyclization. Together with stepwise transborylation with hydroboranes such as pinacolborane HBpin, such fundamental reactions may pave a catalytic way to borane‐induced oligomerization of arylacetylenes and arylallenes.
- Subjects
OLIGOMERIZATION; REARRANGEMENTS (Chemistry); RING formation (Chemistry); HYDROBORATION; ALLYLBORATION; ETHYNYL benzene
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 4, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300839