Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds
The first metal-free catalytic hydroboration of carbonyl derivatives has been developed in which a catalytic amount of 1,3,2-diazaphospholene effectively promotes a hydroboration reaction of aliphatic and aromatic aldehydes and ketones. The reaction mechanism involves the cleavage of both the P-O bo...
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Main Authors: | , , |
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Other Authors: | |
Format: | Article |
Language: | English |
Published: |
2015
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Subjects: | |
Online Access: | https://hdl.handle.net/10356/103939 http://hdl.handle.net/10220/24628 |
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Institution: | Nanyang Technological University |
Language: | English |
Summary: | The first metal-free catalytic hydroboration of carbonyl derivatives has been developed in which a catalytic amount of 1,3,2-diazaphospholene effectively promotes a hydroboration reaction of aliphatic and aromatic aldehydes and ketones. The reaction mechanism involves the cleavage of both the P-O bond of the alkoxyphosphine intermediate and the B-H bond of pinacolborane as well as the formation of P-H and B-O bonds. Thus, the reaction proceeds through a non-metal σ-bond metathesis. Kinetic and computational studies suggest that the σ-bond metathesis occurred in a stepwise but nearly concerted manner. |
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