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The Hidden Role of Boranes and Borohydrides in Hydroboration Catalysis
ACS Catalysis ( IF 12.9 ) Pub Date : 2020-11-04 , DOI: 10.1021/acscatal.0c04051
Andrew D. Bage 1 , Kieran Nicholson 1 , Thomas A. Hunt 2 , Thomas Langer 3 , Stephen P. Thomas 1
Affiliation  

The continued development of hydroboration catalysts typifies the importance of this transformation as a testbed for catalytic activity and as a fundamental reaction for organic synthesis. Catalytic hydroboration studies routinely investigated the decomposition of HBcat but in the case of HBpin, decomposition is not commonly considered because of its perceived stability. Organoboranes catalyze the hydroboration of alkenes and alkynes; these species can be formed from the facile decomposition of 1,3,2-dioxaborolanes (e.g., HBcat and HBpin) by nucleophiles and Lewis acids. Similarly, the nucleophilic decomposition of 1,3,2-dioxaborolanes to borohydride species can catalyze the reduction of carbonyl derivatives. These motifs are abundant in hydroboration catalysis; therefore, the potential for hidden boron catalysis is high and must be controlled for. This Perspective discusses the current methods for probing 1,3,2-dioxaborolane decomposition, highlights the need to consider this hidden catalysis in the future development of hydroboration catalysis, and proposes a set of protocols for the identification of hidden boron catalysis.

中文翻译:

硼烷和硼氢化物在氢硼化催化中的隐藏作用

加氢硼化催化剂的不断发展体现了这种转变作为催化活性试验床和有机合成基本反应的重要性。催化硼氢化研究常规地研究了HBcat的分解,但在HBpin的情况下,由于其可感知的稳定性,因此通常不考虑分解。有机硼烷催化烯烃和炔烃的硼氢化。这些物质可以由亲核试剂和路易斯酸容易地分解1,3,2-二氧杂硼杂环戊烷(例如HBcat和HBpin)形成。类似地,1,3,2-二氧杂硼杂环戊烷的亲核分解为硼氢化物可催化羰基衍生物的还原。这些基序在硼氢化催化中很丰富。因此,隐藏的硼催化的潜力很高,必须加以控制。
更新日期:2020-11-21
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