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1.
Chem Commun (Camb) ; 57(65): 8055-8058, 2021 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-34291778

RESUMO

An efficient Pd-catalysed ß-C(sp3)-H arylation of diverse native amides with aryl iodides was developed. This protocol overcomes the necessity of the Thorpe-Ingold effect and features broad substrate scope and good functional group tolerance. The potential application of this protocol is collectively demonstrated by gram-scale synthesis and the synthesis of several bioactive molecules.

2.
Chem Commun (Camb) ; 57(6): 765-768, 2021 Jan 26.
Artigo em Inglês | MEDLINE | ID: mdl-33355557

RESUMO

Herein, we report a novel strategy to access CH2F-containing ketones through Pd-catalysed ß-selective methyl C(sp3)-H fluorination. The reaction features high regioselectivity and a broad substrate scope, constituting a modular method for the late-stage transformation of the native methyl (CH3) into the monofluoromethyl (CH2F) group.

3.
Org Lett ; 22(21): 8250-8255, 2020 Nov 06.
Artigo em Inglês | MEDLINE | ID: mdl-33075228

RESUMO

Herein we report a novel Cu-catalyzed regioselective C2-H alkylation of benzimidazoles with aromatic alkenes. The reaction features exclusive regioselectivity and broad substrate scope in the intermolecular alkylation of benzimidazoles with terminal and internal aromatic alkenes, constituting a modular access toward benzimidazole-containing 1,1-di(hetero)aryl alkanes. The intramolecular C2-H alkylation of benzimidazoles with aromatic alkenes has been achieved in an endo-selective manner. The enantioselective C2 alkylation of benzimidazoles has also been realized with moderate to good stereocontrol.

4.
Org Biomol Chem ; 18(34): 6732-6737, 2020 09 14.
Artigo em Inglês | MEDLINE | ID: mdl-32832956

RESUMO

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

5.
Org Lett ; 22(6): 2396-2402, 2020 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-32124610

RESUMO

Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter- and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of ß-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo- and regioselectivity.

6.
Chem Commun (Camb) ; 55(96): 14458-14461, 2019 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-31728469

RESUMO

A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.

7.
Chem Commun (Camb) ; 55(49): 7049-7052, 2019 Jun 13.
Artigo em Inglês | MEDLINE | ID: mdl-31143893

RESUMO

A palladium catalyzed selective C(sp3)-H arylation and acetoxylation of alcohols using a practical bidentate auxiliary were developed. Masked alcohols were selectively arylated at the ß-position with diverse aryl iodides for the first time. Moreover, an efficient and site-selective acetoxylation of various primary methyl, methylene, and benzylic C(sp3)-H bonds was performed by using cheap K2S2O8 as the external oxidant.

8.
Angew Chem Int Ed Engl ; 57(43): 14085-14089, 2018 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-30161283

RESUMO

Selective introduction of fluorine into molecules by the cleavage of inert C-H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcohols in organic chemistry as the most ubiquitous building blocks, a versatile and selective C(sp3 )-H and C(sp2 )-H fluorination of simple alcohols, enabled by novel designed exo-directing groups, is described. C(sp2 )-H bond fluorination was achieved by using a simple acetone oxime as auxiliary, whereas a new, modular and easily accessible bidentate auxiliary was developed for the efficient and site-selective fluorination of various primary methyl, methylene, and benzylic C(sp3 )-H bonds. Fluorinated alcohols can readily be accessed by the removal of auxiliaries, and significantly expands the synthetic prospect of the present procedure.

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