Enantiospecific Alkynylation of Alkylboronic Esters

Wang, Yahui; Noble, Adam; Myers, Eddie L.; Aggarwal, Varinder K.

doi:10.1002/ange.201600599

Cited by 35 publications

(8 citation statements)

References 93 publications

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“…As expected, 3c participated in conventional oxidations with NaBO 3 (17) [20] or carbon homologations through the incorporation of an alkene group at the CÀB terminus with Grignard reagents (12) [21] or bromoethylene (13). [22] Thei ntroduction of (hetero)aryl or carbonyl motifs…”

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confidence: 63%

Nickel‐Catalyzed Umpolung Arylation of Ambiphilic α‐Bromoalkyl Boronic Esters

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Martı́n

2018

Angew Chem Int Ed

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A nickel-catalyzed reductive arylation of ambiphilic α-bromoalkyl boronic esters with aryl halides is described. This platform provides an unrecognized opportunity to promote the catalytic umpolung reactivity of ambiphilic reagents with aryl halides, thus unlocking a new cross-coupling strategy that complements existing methods for the preparation of densely functionalized alkyl-substituted organometallic reagents from simple and readily accessible precursors.

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confidence: 63%

Nickel‐Catalyzed Umpolung Arylation of Ambiphilic α‐Bromoalkyl Boronic Esters

Sun

Martı́n

2018

Angew Chem Int Ed

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“…We propose that Zn(OTf) 2 coordinates effectively with a carbonyl group of the N-succinimide (NHS) unit, thus enhancing the interaction between the positive iodine and alkene and, therefore, shortening the reaction time dramatically. Inferior reaction performance was observed using other zinc catalysts, such as ZnCl 2 , Table 1, entries [13][14][15]. With the optimized conditions in hand, we explored the scope of zinc-catalysed N 2 -b-iodoalkylation reaction by varying the structure of alkenes.…”

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confidence: 99%

Zinc‐Catalysed N‐Iodosuccinimide‐Enabled Selective N²‐Olefination of Benzotriazoles with Alkenes

et al. 2019

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Herein, we describe a zinc-catalysed N 2 -selective olefination of benzotriazoles with unactivated alkenes and styrenes. The transformation is achieved by a N-iodosuccinimide (NIS)-mediated two-step, onepot approach, proceeding through sequential regioselective b-iodoalkylation of benzotriazoles with alkenes and a subsequent base-promoted 1,2-elimination. The N 2 -selective b-iodoalkylation of benzotriazoles is highly stereospecific and works under very simple and mild conditions, exhibiting excellent functional group tolerance. The high N 2 -selectivity is attributed to intermolecular hydrogen bonding between the Niodosuccinimide and the NH hydrogen bond donor at the 1-position of the benzotriazoles. This scalable process, serving as an efficient method for modular assembly of structurally diverse N 2 -olefinated benzotriazoles, will significantly contribute to the chemistry of N 2 -functionization of benzotriazoles.

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“…As initially anticipated, a canonical oxidation with NaBO 3 cleanly delivered 11 in good yields. [22] Likewise, a series of CÀC bond-forming reactions could easily be conducted via CÀB bond cleavage in 4 r, including Pdcatalyzed Suzuki-Miyaura reactions (9), [23] or the incorpora-tion of heterocycles (8), [24] vinyl halides (10), [25] or ketone backbones (6, 7) [26,27] in one-pot procedures. Taken together, the data shown in Schemes 4-6 serves as a testament to the prospective impact of our 1,2-difunctionalization method.…”

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confidence: 99%