Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation.

نویسندگان

  • Xiao-Yun Deng
  • Jin-Hong Lin
  • Jian Zheng
  • Ji-Chang Xiao
چکیده

Difluoromethylation of the activated X-H bond (X = N, O and S) and aliphatic thiols, and gem-difluorocyclopropenation of alkynes with difluorocarbene generated in situ from difluoromethylene phosphobetaine (Ph3P(+)CF2CO2(-)) by decarboxylation occurred smoothly without the presence of any base or other additives.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: a new difluoromethylation reagent for S-, N-, and C-nucleophiles.

The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF(2)H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethy...

متن کامل

A new method for the synthesis of difluoromethyl enol ethers by O-difluoromethylation of 1,3-diones with ClCF2CO2Et.

A facile, efficient, single-step protocol for the synthesis of difluoromethyl enol ether derivatives by O-difluoromethylation of 1,3-diones via in situ generation of difluorocarbene from ClCF2CO2Et has been developed. The functional group tolerance, scalability of the reaction, and mild reaction conditions make it an attractive protocol for the synthesis of biologically relevant difluoromethyl ...

متن کامل

2-Chloro-2,2-difluoroacetophenone: a non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives.

A novel and non-ODS-based (ODS = ozone-depleting substance) preparation of 2-chloro-2,2-difluoroacetophenone (1) was achieved in high yield by using 2,2,2-trifluoroacetophenone as the starting material. Compound 1 was found to act as a good difluorocarbene reagent, which readily reacts with a variety of structurally diverse phenol derivatives 4 in the presence of potassium hydroxide or potassiu...

متن کامل

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes

α,α-Difluoro-substituted organozinc reagents generated from conventional organozinc compounds and difluorocarbene couple with 1-bromoalkynes affording gem-difluorinated alkynes. The cross-coupling proceeds in the presence of catalytic amounts of copper iodide in dimethylformamide under ligand-free conditions.

متن کامل

Efficient Difluoromethylation of sp3 Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases

Introduction of a difluoromethyl (CF2H) unit into organic molecules is of specific interest in medicinal chemistry and chemical biology, as compounds with a CF2H moiety can act as an isostere to molecules having a methanol (CH2OH) unit with improved lipophilicity. Among several strategies for the synthesis of CF2H compounds available, a late-stage difluoromethylation using easy-to-handle reagen...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Chemical communications

دوره 51 42  شماره 

صفحات  -

تاریخ انتشار 2015