Switchable Palladium-Catalyst Reaction of Bromomethyl Sulfoxides, CO, and N-Nucleophiles: Aminocarbonylation at Csp3 versus Oxidative Carbonylation of Amines
Cristian Mollar; Carmen Ramirez de Arellano; Mercedes Medio-Simón; Gregorio Asensio; Journal of Organic Chemistry 77 (2012) 9693–9701; doi:10.1021/jo301778n

data_4027671
_publ_section_title
;
 Switchable Palladium-Catalyst Reaction of Bromomethyl Sulfoxides, CO, and
 N-Nucleophiles: Aminocarbonylation at Csp3 versus Oxidative Carbonylation
 of Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9693
_journal_page_last               9701
_journal_paper_doi               10.1021/jo301778n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C13 H17 N O2 S'
_chemical_formula_weight         251.34
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6171(4)
_cell_length_b                   8.6157(8)
_cell_length_c                   26.290(3)
_cell_measurement_reflns_used    2108
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.9437
_cell_measurement_theta_min      2.8212
_cell_volume                     1272.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171 (Agilent Tec., 2012)'
_computing_data_collection       'CrysAlisPro 1.171 (Agilent Tec., 2012)'
_computing_data_reduction        'CrysAlisPro 1.171 (Agilent Tec., 2012)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Oxfor Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6964
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.01
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.1270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                3461
_reflns_number_total             3716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301778n_si_001.cif
_cod_data_source_block           ascm131_comp_(R)_3be
_cod_database_code               4027671