N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system

• Zhang-Guo Zheng,
• Jun Wen,
• Na Wang,
• Bo Wu and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2008, 4, No. 40, doi:10.3762/bjoc.4.40

• , imides and sulfonamides catalyzed by a copper salt/EtOH system has been developed. In the absence of a base or additive the corresponding N-arylation products were obtained in moderate to excellent yields. Keywords: N-arylation; arylboroxine; copper salt; cross-coupling; ethanol; Introduction The

• ). Furthermore, we expand the substrate scope of this reaction: a variety of amines, amides, imides and sulfonamides with arylboroxine can also participate in this catalytic system to give the corresponding N-arylation products in moderate to excellent yields. To the best of our knowledge, N-arylation of NH

• reaction. In an endeavor to expand the scope of the above methodology, the catalytic system was also applied to imides, amines, amides and sulfonamides. Such coupling was found to give the desired N-arylation products in moderate yields, as shown in Table 5, except for sulfonamide, which afforded the

The enantiospecific synthesis of (+)-monomorine I using a 5-endo- trig cyclisation strategy

• Malcolm B. Berry,
• Donald Craig,
• Philip S. Jones and
• Gareth J. Rowlands

Beilstein J. Org. Chem. 2007, 3, No. 39, doi:10.1186/1860-5397-3-39

• tosyl moiety as the nitrogen-protecting group (PG) and resulted in a succinct synthesis of alkenes of the type 4 (X = NTs; Scheme 1). [15] Disappointingly, all attempts to ring-close the sulfonamides proved fruitless, and it was found that desulfonylation was necessary before cyclisation could be

Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

• Olga García Mancheño and
• Carsten Bolm

Beilstein J. Org. Chem. 2007, 3, No. 25, doi:10.1186/1860-5397-3-25

• % yield. Conclusion A convenient alternative procedure for the synthesis of sulfonimidamides from sulfinamides and various amines and sulfonamides using N-chlorosuccinimide as halogenating agent has been developed. Introduction Sulfonimidamides 3 are derivatives of sulfonic acid and analogous of

• sulfonamides, in which one oxygen has been replaced by a nitrogen group. They are known since 1962,[1] and a number of recent investigations focussed on both their reactivity and application in organic synthesis, such as nitrogen sources for metal-catalyzed nitrene transfer reactions, [2][3][4][5] and their