In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide: scalable synthesis of alkynes from aldehydes

TY - JOUR

T1 - In situ generation of the Ohira-Bestmann Reagent from stable sulfonyl azide

T2 - scalable synthesis of alkynes from aldehydes

AU - Jepsen, Tue Heesgaard

AU - Kristensen, Jesper Langgaard

PY - 2014/10/3

Y1 - 2014/10/3

N2 - We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.

AB - We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.

U2 - 10.1021/jo501803f

DO - 10.1021/jo501803f

M3 - Journal article

C2 - 25215450

SN - 0022-3263

VL - 79

SP - 9423

EP - 9426

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -