Direct Production of Enaminones from Terminal Alkynes via Rhodium-Catalyzed Reaction of Formamides with N-Sulfonyl-1,2,3-triazoles.
Miura, Tomoya; Funakoshi, Yuuta; Tanaka, Takamasa; Murakami, Masahiro; Organic letters 16 (2014) 2760–2763; doi:10.1021/ol5010774

data_1515759
_publ_section_title
;
 Direct Production of Enaminones from Terminal Alkynes via
 Rhodium-Catalyzed Reaction of Formamides with N-Sulfonyl-1,2,3-triazoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2760
_journal_page_last               2763
_journal_paper_doi               10.1021/ol5010774
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C18 H20 N2 O3 S'
_chemical_formula_weight         344.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.988(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5437(6)
_cell_length_b                   22.8556(14)
_cell_length_c                   9.3763(7)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.03
_cell_volume                     1776.6(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16278
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.8727
_exptl_absorpt_correction_T_min  0.8564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.70
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.4581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                3209
_reflns_number_total             4068
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5010774_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1515759.cif.'
_cod_original_sg_symbol_Hall     -p_2yn
_cod_original_sg_symbol_H-M      p_21/n
_cod_database_code               1515759