Literature DB >> 31822876

Iridium-catalyzed B-H insertion of sulfoxonium ylides and borane adducts: a versatile platform to α-boryl carbonyls.

Shang-Shi Zhang1, Hui Xie2, Bing Shu3, Tong Che2, Xiao-Tong Wang3, Dongming Peng4, Fan Yang2, Luyong Zhang1.   

Abstract

Iridium-catalyzed boron-hydrogen bond insertion reactions of trimethylamine-borane and sulfoxonium ylides have been demonstrated, furnishing α-boryl ketones in moderate to excellent yields in most cases (51 examples; up to 84%). This practical and scalable insertion reaction showed broad substrate scope, high functional-group compatibility and could be applied in late-stage modification of structurally complex drug compounds. Further synthetic applications were also demonstrated.

Entities:  

Year:  2019        PMID: 31822876     DOI: 10.1039/c9cc08795h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  2 in total

Review 1.  Uncommon carbene insertion reactions.

Authors:  Ming-Yao Huang; Shou-Fei Zhu
Journal:  Chem Sci       Date:  2021-11-02       Impact factor: 9.825

Review 2.  Asymmetric transformations from sulfoxonium ylides.

Authors:  Clarice A D Caiuby; Lucas G Furniel; Antonio C B Burtoloso
Journal:  Chem Sci       Date:  2021-12-08       Impact factor: 9.825

  2 in total

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