Intramolecular hydroxycarbene C–H-insertion: The curious case of (o-methoxyphenyl)hydroxycarbene

• Dennis Gerbig,
• David Ley,
• Hans Peter Reisenauer and
• Peter R. Schreiner

Beilstein J. Org. Chem. 2010, 6, 1061–1069, doi:10.3762/bjoc.6.121

• . Hence, the general reactivity pattern of 5 under HVFP conditions is similar to that of other hetereocarbenes. However, synthetic access to substituted 2,3-dihydrobenzofuran derivatives through the in situ generation of various (o-methoxyphenyl)hydroxycarbenes from (o-methoxyphenyl)glyoxylic acids in

CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃

• Julien Monot,
• Louis Fensterbank,
• Max Malacria,
• Emmanuel Lacôte,
• Steven J. Geib and
• Dennis P. Curran

Beilstein J. Org. Chem. 2010, 6, 709–712, doi:10.3762/bjoc.6.82

• (top) and 3b (bottom). Synthesis of stable CAAC–BF3 complexes 3a and 3b and in situ generation of CAAC–BH3 complex 4a. Supporting Information Supporting Information File 118: Procedures and characterization of the new complexes. Supporting Information File 119: Cif file of crystal structure of

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• -(trifluoromethoxy)biphenylyl-2′-diazonium salts such as 19a (R=H) through in situ generation of a trifluoromethyloxonium salt. The yield of trifluoromethylated products was highly dependent on the counteranion as observed in the trifluoromethylation of phenol (Scheme 17) [23]. The synthetic application of thermally

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

• Faiz Ahmed Khan and
• Karuppasamy Parasuraman

Beilstein J. Org. Chem. 2010, 6, No. 64, doi:10.3762/bjoc.6.64

• derivatives; ruthenium; 3-sulfolene; Introduction 3-Sulfolene is a nonflammable, nontoxic, nonhygroscopic and stable crystalline solid and is a convenient equivalent for gaseous 1,3-butadiene [1][2][3] and is commonly used for in situ generation of 1,3-butadiene as the diene component in Diels–Alder

One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

• Priyabrata Roy and
• Binay Krishna Ghorai

Beilstein J. Org. Chem. 2010, 6, No. 52, doi:10.3762/bjoc.6.52

• trapped through Diels–Alder reaction with dienophiles leading to the synthesis of nitrogen containing heterocyclic analogues of quinoxaline and phenazine, respectively, in one-pot. This is the first report of in situ generation of furo[3,4-b]pyrazine intermediates. Synthetic plan towards quinoxaline

Controlling hazardous chemicals in microreactors: Synthesis with iodine azide

• Johan C. Brandt and
• Thomas Wirth

Beilstein J. Org. Chem. 2009, 5, No. 30, doi:10.3762/bjoc.5.30

• stable carbamoyl azides 4 as shown in Scheme 1. As sodium azide is poorly soluble in organic solvents, we decided to use tetrabutylammonium azide for the in situ generation of iodine azide. The reaction with iodine monochloride is rapid and after several minutes (depending on the flow rate) the aldehyde

• , 2H, H-12), 0.95 (t, 3JHH = 7.4 Hz, 3H, H-13) ppm; 13C NMR (125 MHz, CDCl3): δ 171.3 (C-8), 137.9 (C-5), 129.0 (C1/C-3), 124.2 (C-2), 119.7 (C-4/C-6), 37.6 (C-10), 27.7 (C-11), 22.4 (C-12), 13.8 (C-13) ppm. Microreactor setup for the in situ generation and use of iodine azide (IN3). Azide addition to

Ru-catalyzed dehydrogenative coupling of carboxylic acids and silanes - a new method for the preparation of silyl ester

• Guo-Bin Liu and
• Hong-Yun Zhao

Beilstein J. Org. Chem. 2008, 4, No. 27, doi:10.3762/bjoc.4.27

• )3Cl [46] and promoted by organocatalyst such as triphenylphosphine [47]. Generally, catalysts such as transition metals are expensive. [CuH(Ph3P)] requires a multiple-step synthetic approach and in-situ generation protocols. Results and Discussion In this communication, we wish to report the first

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• resulted in us developing a one-pot methodology involving its in situ generation. We have recently demonstrated the applicability of N-protected-4-methoxy-2-trimethylsilyloxy pyrroles 5 to the synthesis of key intermediates for the alkaloids lepadiformine [10] and castanospermine [11] using vinylogous