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1.
Org Lett ; 26(29): 6174-6178, 2024 Jul 26.
Article in English | MEDLINE | ID: mdl-39018357

ABSTRACT

A Pd-catalyzed regioselective hydrocarboxylation of alkyl terminal olefins with oxalic acid is described. A wide variety of linear carboxylic acids can be readily obtained in good yields and high l/b (linear/branched) ratios with Pd2(dba)3 and (p-ClPh)3P under mild conditions. The reaction process is operationally simple and requires no handling of toxic CO. In addition, branched carboxylic acids can also be formed in good regioselectivities with PdCl2 and (2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)diphenylphosphine (L1).

2.
Org Lett ; 25(43): 7786-7790, 2023 Nov 03.
Article in English | MEDLINE | ID: mdl-37856251

ABSTRACT

A regioselective Pd-catalyzed hydrocarboxylation of vinyl arenes with oxalic acid is described. A wide variety of either linear or branched carboxylic acids can be readily obtained with high regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO. Besides the ligand, the counteranion of the Pd catalyst system plays an important role in the regioselectivity.

3.
Org Lett ; 25(39): 7176-7180, 2023 Oct 06.
Article in English | MEDLINE | ID: mdl-37755340

ABSTRACT

An effective Pd-catalyzed regioselective hydroformylation process with N-formylsaccharin or 2,4,6-trichlorophenyl formate along with formic acid is described. Linear aldehydes can be obtained in up to 83% yield and >20:1 l/b ratio. The reaction is operationally simple without the need for external CO and H2.

4.
Org Lett ; 25(12): 2006-2011, 2023 Mar 31.
Article in English | MEDLINE | ID: mdl-36926923

ABSTRACT

This work describes an efficient Pd-catalyzed ortho-C-H amination of N-(quinolin-8-yl)benzamides with di-t-butyldiaziridinone, providing a variety of anthranilic amides in good yields. The reaction likely involves the formation of a pallada(II)heterocycle via aryl C-H activation and subsequent amination with di-t-butyldiaziridinone.

5.
Chem Soc Rev ; 51(15): 6757-6773, 2022 Aug 01.
Article in English | MEDLINE | ID: mdl-35852221

ABSTRACT

Hydrocarboxylation, hydroesterification, and hydroamidation of olefins are fundamental transformations in organic synthesis. Asymmetric processes for these transformations provide an effective and straightforward approach to optically active carboxylic acids and their derivatives, which are highly useful compounds in pharmaceuticals, materials, fine chemicals, etc. This review provides a brief summary of the development of asymmetric hydroesterification, hydrocarboxylation, and hydroamidation with CO and its surrogates.


Subject(s)
Alkenes , Transition Elements , Alkenes/chemistry , Carboxylic Acids , Catalysis , Chemistry Techniques, Synthetic , Transition Elements/chemistry
6.
Org Lett ; 24(3): 886-891, 2022 Jan 28.
Article in English | MEDLINE | ID: mdl-35029395

ABSTRACT

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

7.
Org Lett ; 23(22): 8958-8962, 2021 11 19.
Article in English | MEDLINE | ID: mdl-34756047

ABSTRACT

A novel Cu-promoted C-N coupling between boron esters and di-tert-butyldiaziridinone is described. A wide variety of aryl ureas can be readily obtained under mild conditions with up to a 92% yield.

8.
Org Lett ; 23(18): 7118-7122, 2021 09 17.
Article in English | MEDLINE | ID: mdl-34491766

ABSTRACT

An efficient tandem nucleophilic aminopalladation and carbene insertion sequence is described for the synthesis of indole fused polycycles. The reaction process provides a variety of substituted indeno[1,2-b]indoles in up to 99% yields.


Subject(s)
Indoles/chemistry , Methane/analogs & derivatives , Polycyclic Compounds/chemical synthesis , Cyclization , Indoles/chemical synthesis , Methane/chemistry , Molecular Structure , Polycyclic Compounds/chemistry
9.
Org Lett ; 23(19): 7561-7565, 2021 10 01.
Article in English | MEDLINE | ID: mdl-34523937

ABSTRACT

This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.

10.
Org Lett ; 23(9): 3646-3651, 2021 05 07.
Article in English | MEDLINE | ID: mdl-33861616

ABSTRACT

Indoles are an important class of molecules. This paper describes an efficient palladium-catalyzed synthesis of indoles from 2-iodostyrenes and di-t-butyldiaziridinone with a simultaneous installation of two C-N bonds. The reaction process likely proceeds through the oxidative insertion of Pd to aryl iodide and subsequent vinyl C-H activation to from a pallada(II)cycle intermediate, which is bisaminated by di-t-butyldiaziridinone to give the indole product.

11.
Org Lett ; 23(9): 3237-3242, 2021 05 07.
Article in English | MEDLINE | ID: mdl-33886335

ABSTRACT

Palladium-catalyzed C-N bond formation is one of the widely used transformations for the synthesis of structurally diverse N-heterocycles. This work describes an efficient palladium-catalyzed multiple-C-N bond formation reaction for the synthesis of highly π-conjugated N-heterocycles, indolo[3,2-b]indoles with di-tert-butyldiaziridinone. The reaction likely proceeds through the initial formation of an indole-fused palladacycle by nucleophilic aminopalladation and subsequent bisamination to give indolo[3,2-b]indoles.

12.
RSC Adv ; 11(22): 13040-13046, 2021 Apr 07.
Article in English | MEDLINE | ID: mdl-35423889

ABSTRACT

This work describes an effective enantioselective bromohydroxylation of cinnamyl alcohols with (DHQD)2PHAL as the catalyst and H2O as the nucleophile, providing a variety of corresponding optically active bromohydrins with up to 95% ee.

13.
Org Lett ; 22(5): 1868-1873, 2020 Mar 06.
Article in English | MEDLINE | ID: mdl-32043881

ABSTRACT

An effective Pd-catalyzed isomerization of olefins with 2-PyPPh2 as the ligand is described. A wide variety of trans-2-olefins bearing various functional groups can be obtained with high regio- and stereoselectivity under mild reaction conditions. The ligand is crucial for the reaction.

14.
Cancer Nurs ; 43(6): 455-467, 2020.
Article in English | MEDLINE | ID: mdl-31464692

ABSTRACT

BACKGROUND: Peripherally inserted central catheters (PICCs) and implantable port catheters (IPCs) are 2 most common central venous access for cancer patients receiving chemotherapy. However, no specific evidence exists to guide practitioners on safety and less cost. OBJECTIVE: To compare the differences of complications and costs of PICC and IPC in the treatment of cancer patients with chemotherapy and to provide a basis for better clinical decision making. METHODS: All the cohort studies were searched in the Cochrane Library, JBI, PubMed, Elsevier, Web of Science, CINAHL, CBM, and CNKI from inception to July 2018. Two reviewers screened and selected trials, evaluated quality, and extracted data. Meta-analysis and description of the outcomes were performed by using the RevMan 5.3 software. RESULTS: A total of 761 articles were retrieved, with 15 articles meeting eligibility criteria. Outcome analysis showed no difference in 1-puncture success rate. Peripherally inserted central catheter use was associated with higher complication rates than IPC, including occlusion, infection, malposition, catheter-related thrombosis, extravasation, phlebitis, and accidental removal rate. The life span of IPC was longer than that of PICC, and the costs of IPC were lower. CONCLUSIONS: Implantable port catheter has advantages over PICC in reducing cancer patients' complications and less cost in terms of long-term cancer chemotherapy. IMPLICATIONS FOR PRACTICE: In terms of safety, the results provide evidence for practitioners to choose which type of central venous catheters is better for cancer chemotherapy patients. In terms of costs, practitioners need to make decisions about which type of central venous catheters has less cost.


Subject(s)
Catheters, Indwelling/adverse effects , Catheters, Indwelling/economics , Central Venous Catheters/adverse effects , Central Venous Catheters/economics , Neoplasms/drug therapy , Neoplasms/economics , Adult , Aged , Aged, 80 and over , Cohort Studies , Female , Humans , Male , Middle Aged
15.
Org Lett ; 21(15): 5967-5970, 2019 Aug 02.
Article in English | MEDLINE | ID: mdl-31298860

ABSTRACT

An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

16.
Org Biomol Chem ; 17(29): 6998-7001, 2019 07 24.
Article in English | MEDLINE | ID: mdl-31304944

ABSTRACT

A novel and efficient Cu(i)-catalyzed homo-coupling of indanone derivatives using diaziridinone as an oxidant is described. A variety of 1,4-dicarbonyl compounds bearing two adjacent quaternary stereocenters were obtained in high yields with high diastereoselectivities via a base-free and operationally simple process under mild reaction conditions.


Subject(s)
Aziridines/chemistry , Coordination Complexes/chemistry , Copper/chemistry , Indans/chemical synthesis , Catalysis , Indans/chemistry , Molecular Structure , Stereoisomerism
17.
Org Lett ; 21(13): 5157-5161, 2019 07 05.
Article in English | MEDLINE | ID: mdl-31247760

ABSTRACT

A novel Pd-catalyzed oxidative Heck reaction with readily available Grignard reagents using di- t-butyldiaziridinone as an oxidant has been developed. Various substituted olefins were obtained in 46-91% yields with high regioselectivity under mild reaction conditions.


Subject(s)
Diazomethane/chemistry , Oxidants/chemistry , Palladium/chemistry , Catalysis , Oxidation-Reduction
18.
Org Lett ; 19(7): 1748-1751, 2017 04 07.
Article in English | MEDLINE | ID: mdl-28345924

ABSTRACT

An effective Pd-catalyzed hydrocarboxylation of aryl olefins with Ac2O and formic acid is described. A variety of 2- and 3-arylpropanoic acids can be regioselectively formed by the judicious choice of ligand without the use of toxic CO gas.

19.
Org Lett ; 18(21): 5456-5459, 2016 11 04.
Article in English | MEDLINE | ID: mdl-27779413

ABSTRACT

An effective Pd-catalyzed regio- and enantioselective hydroesterification of aryl olefins with phenyl formate is described. A variety of phenyl 2-arylpropanoates can be obtained in good yields with high b/l ratios and ee's without using toxic CO gas.

20.
J Am Chem Soc ; 138(45): 14864-14867, 2016 11 16.
Article in English | MEDLINE | ID: mdl-27797184

ABSTRACT

An effective palladium-catalyzed regioselective hydroformylation of olefins with formic acid is described. The ligand plays a crucial role in directing the reaction pathway. Linear aldehydes can be obtained in up to 93% yield with >20:1 regioselectivity using 1,3-bis(diphenylphosphino)propane (dppp) as the ligand. The reaction process is operationally simple and requires no syngas.

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