Synthesis of allylic sulfones
Formation of allyl phenyl sulfones with excellent yields from allylic alcohols was promoted by a combination of Pd(OAc)2, PPh3, and Et3B via in situ activation of the alcohol group.
S. Chandrasekhar, V. Jagadeshwar, B. Saritha, C. Narsihmulu, J. Org. Chem., 2005, 70, 6506-6507.
In the presence of a Pd catalyst and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Use of BINOL as a ligand allowed the transformation of unsymmetric α-chiral primary allylic amines in good to excellent yields with excellent retention of ee.
X.-S. Wu, Y. Chen, M.-B. Li, M.-G. Zhou, S.-K. Tian, J. Am. Chem. Soc., 2012, 134, 14694-14697.
A Rh(I)/DPEphos/benzoic acid catalyst system enables the transformation of terminal alkynes with sulfonyl hydrazides to produce branched allylic sulfones with very good yields and selectivities.
K. Xu, V. Khakyzadeh, T. Bury, B. Breit, J. Am. Chem. Soc., 2014, 136, 16124-16127.
The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, which can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums to give sulfone products.
A. S. Deeming, C. J. Russell, A. J. Henessy, M. C. Willis, Org. Lett., 2014, 16, 150-153.
An iridium-catalyzed allylation of various sodium sulfinates with achiral allylic carbonates occurs in good yields, with high selectivity for the branched isomer, and high enantioselectivities (up to 98% ee).
M. Ueda, J. F. Hartwig, Org. Lett., 2010, 12, 88-91.
An iodine-catalyzed functionalization of various olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC provides highy valuable vinyl, allyl, and β-iodo vinylsulfones. This simple, efficient, and environmentally benign approach is attractive to both synthetic and medicinal chemistry.
L. Kadari, R. K. Palakodety, L. P. Yallapragada, Org. Lett., 2017, 19, 2580-2583.
A one-pot synthesis of aryl sulfones from primary alcohols is described. Alcohols were treated with N-bromosuccinimide and triphenylphosphine, followed by addition of sodium arenesulfinate with a catalytic amount of tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.
T. Murakami, K. Furusawa, Synthesis, 2002, 479-482.
In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields. A catalysis with byproduct HCl is involved in this new protocol.
H.-H. Li, D.-J. Dong, Y.-H. Jin, S.-K. Tian, J. Org. Chem., 2009, 74, 9501-9504.