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Base‐Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium‐Catalyzed Cross‐Coupling Reactions
Author(s) -
Cook Xinlan A. F.,
Pantaine Loïc R. E.,
Blakemore David C.,
Moses Ian B.,
Sach Neal W.,
Shavnya Andre,
Willis Michael C.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202109146
Subject(s) - nucleophile , chemistry , aryl , reagent , palladium , catalysis , combinatorial chemistry , nitrile , coupling reaction , substrate (aquarium) , salt (chemistry) , organic chemistry , alkyl , oceanography , geology
Heteroaromatic sulfinates are effective nucleophilic reagents in Pd 0 ‐catalyzed cross‐coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi‐step transformations. Here we introduce base‐activated, latent sulfinate reagents: β‐nitrile and β‐ester sulfones. We show that under the cross‐coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium‐catalyzed desulfinative cross‐coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi‐step substrate elaboration, and amenable to scale‐up.